反应检索

Published experimental reaction records / 已发表实验反应记录

Selected source-linked experiments are available below; the live search also queries the Open Reaction Database.

以下为可直接读取的来源实验记录；实时检索同时连接 Open Reaction Database。

1. Suzuki–Miyaura cross-coupling: 2-Chloropyridine + N-Boc-2-pyrroleboronic acid → tert-butyl 2-(pyridin-2-yl)-1H-pyrrole-1-carboxylate

   Temperature: 65.3 °C; Time: 600 second

   10.1039/C6RE00153J · ORD ord-00d7e52b7059428ba267697c34497f96

2. Suzuki–Miyaura cross-coupling: 3-bromoquinoline + 3,5-Dimethylisoxazole-4-boronic acid pinacol ester → 3,5-dimethyl-4-(quinolin-3-yl)isoxazole

   Temperature: 110 °C; Time: 166.5 second

   10.1039/C6RE00153J · ORD ord-058a3137f3e54649b663eca49d7b37d8

3. Copper-catalyzed hydroamination preparation: N,N-dibenzylhydroxylamine + pivaloyl chloride → N,N-Dibenzyl-O-pivaloylhydroxylamine

   Temperature: 0 °C; Time: 6 hour; Atmosphere: dry nitrogen

   10.15227/orgsyn.095.0080 · ORD ord-352807a1f4c14595afeef50c6c39ae38

4. Sulfonamide synthesis: Aniline + C8H9ClO4S · ORD RSJSYCZYQNJQPY-UHFFFAOYSA-N → C14H15NO4S · ORD CVQXOCMYHLBICI-UHFFFAOYSA-N

   Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

   10.1021/co400012m · ORD ord-19c66ae2f44e4fd0b01fdcb94df9e008

5. Decarboxylative sp3–sp2 cross-coupling: Boc-Pip-OH + 1-acetyl-4-bromobenzene → C18H25NO3 · ORD ZSYSIHPTMRWZKU-UHFFFAOYSA-N

   Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

   10.1126/science.1255525 · ORD ord-153de2a96e07484e93d525d81f966789

6. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H11Cl · ORD DPHXNOVRXVINNX-MRVPVSSYSA-N → C18H20O · ORD STXDYXZNZMIPSJ-KIUWMYQTSA-N

   Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

   10.1021/acscatal.9b01785 · ORD ord-0350268a675b4c5188d89b774435bc01

7. Borylation: C13H14N2 · ORD DFEZHELNRPACHC-UHFFFAOYSA-N → C19H25BN2O2 · ORD OZRMFWAMCXLUTR-UHFFFAOYSA-N

   Temperature: 80 °C; Time: 24 hour; Atmosphere: argon

   10.1002/anie.201104544 · ORD ord-04ef4005b699487e9a1d97d3cb0cd4bf

8. Nickel-catalyzed cross-coupling: C13H22O3Si · ORD FGLFSDHJENOLAP-UHFFFAOYSA-N + C15H18N2O2 · ORD NKZBKHMNDKJNFZ-UHFFFAOYSA-N → C19H19N · ORD FAYPFKWLDJARFS-UHFFFAOYSA-N

   Temperature: 120 °C; Time: 12 hour

   10.1002/adsc.201600590 · ORD ord-02afb49d4df44df49cf67a3f3e752e4c

9. Minisci alkylation: Caffeine + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C14H20N4O2 · ORD HJRNYGSEKWPIMR-UHFFFAOYSA-N

   Temperature: 40 °C; Time: 40 hour; Atmosphere: argon

   10.1021/acs.orglett.8b02988 · ORD ord-033e08aa68b44b43a0ff24b3848fef33

10. Copper-catalyzed hydroamination preparation: N,N-Dibenzyl-O-pivaloylhydroxylamine + trans-β-methylstyrene → (R)-N,N-Dibenzyl-1-phenylpropan-1-amine

    Temperature: 23 °C; Time: 12 hour; Atmosphere: dry nitrogen

    10.15227/orgsyn.095.0080 · ORD ord-7b927700e3414788865b46a4d4b18c44

11. Sulfonamide synthesis: Aniline + C8H7ClO3S · ORD FXVDNCRTKXMSEZ-UHFFFAOYSA-N → C14H13NO3S · ORD SWOITTWWCRUZRI-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-1c6755576a944b9aa3ff773d1d98e2d7

12. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-acetyl-4-bromobenzene → C17H23NO3 · ORD FWQTVASVJHZRBU-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-1f43094f0193449f99fdc475f687ddf0

13. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H9Cl · ORD WLJXUWKOEVKMGD-SECBINFHSA-N → C18H18O · ORD DOJXJKJKDFQWLV-YXMGTMDOSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-05854e6497764b88a306b2599d650ad5

14. Borylation: C8H15NO2 · ORD WFFGQLYKMWGXMU-UHFFFAOYSA-N → C14H26BNO4 · ORD AQEITQBMKRPRMU-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 18 hour; Atmosphere: nitrogen

    10.1002/anie.201409186 · ORD ord-190a675c8ccc43a0837566a15ce408f6

15. Nickel-catalyzed cross-coupling: C12H16O2 · ORD LYHJECZUEZOABA-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C17H18 · ORD QEZMSFVMIVYNEK-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 15 hour

    10.1002/anie.200453765 · ORD ord-0021943c24784c9298710a97140aec6d

16. Minisci alkylation: Caffeine + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C9H10F2N4O2 · ORD CHTVRSPUJYGRHE-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 18 hour; Atmosphere: air

    10.1021/ja211422g · ORD ord-70621d6e847749238d95b20c12b2218f

17. Copper-catalyzed hydroamination preparation: 2,3,3-trimethyl-1-butene + N,N-Dibenzyl-O-pivaloylhydroxylamine → (R)-N,N-Dibenzyl-2,3,3-trimethylbutan-1-amine

    Temperature: 40 °C; Time: 12 hour; Atmosphere: dry nitrogen

    10.15227/orgsyn.095.0080 · ORD ord-e5c44ec1b5164f8ea077cf3b7ee0214a

18. Sulfonamide synthesis: Aniline + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C15H17NO2S · ORD ARIRERZAGIDHFR-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-20cbbcbea787416a9b8da637a079260d

19. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-bromo,3-fluoro,4-cyanobenzene → C16H19FN2O2 · ORD ZMGHHTJDLYHHHR-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-21154a43c29b4013be1bcc71ce9e0b68

20. Electroreductive cross-coupling: C10H17Br · ORD FLMHWDCHCOMUPL-JARNTUPDSA-N + C9H11ClO · ORD YOANFEVQVLUDDA-UHFFFAOYSA-N → C19H28O · ORD AZIFVEFTPXTRDO-CPQFKCLQSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-06a027dd80014e70abbb3f824f7c5e16

21. Borylation: C15H14F7NO · ORD MRUQICSSUXUZLL-UHFFFAOYSA-N → C21H25BF7NO3 · ORD XZMHLKDCKNBMLU-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 15 hour; Atmosphere: oxygen

    10.1002/anie.201509996 · ORD ord-03bb8ab8112a4d7a8c80e549cdb4d351

22. Nickel-catalyzed cross-coupling: C11H15BO2 · ORD FQMSNYZDFMWLGC-UHFFFAOYSA-N + C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 12 hour

    10.1002/anie.200801447 · ORD ord-0ad0cf48e9fc46f884313aa14fde7138

23. Minisci alkylation: C7H5NS · ORD IOJUPLGTWVMSFF-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C10H9NOS · ORD RXGAKSUSOSNZKH-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 2 hour; Atmosphere: air

    10.1021/jo9010624 · ORD ord-065a25a8e27e42e0a91bfb691ac92afa

24. Sulfonamide synthesis: Aniline + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C12H10N2O4S · ORD BJKNXDSKYOQVTJ-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-2d9744b45378425790df1ae6c2ee2c57

25. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-bromo,3,5-di(trifluoromethyl)benzene → C17H19F6NO2 · ORD YKEARFAETXFSGJ-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-31999cf4be6346ce9db433cd33193fec

26. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H11Cl · ORD FVHALAXAXLCMOY-MRVPVSSYSA-N → C18H20O · ORD YYABBJFRVGZEMX-HVHJFMEUSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-271d3250a2374b1f9b467b9d1741607e

27. Borylation: C9H12S · ORD DSDAKTYVXFUEEM-UHFFFAOYSA-N → C15H23BO2S · ORD DXFMUBIMBULQSG-UHFFFAOYSA-N

    Temperature: 55 °C; Time: 24 hour; Atmosphere: nitrogen

    10.1002/anie.201610041 · ORD ord-07735c61c2ba4303a5458fefe94b7ddd

28. Nickel-catalyzed cross-coupling: Morpholine + C13H12O2 · ORD VTXLTXPNXYLCQD-UHFFFAOYSA-N → C10H13NO · ORD FHQRDEDZJIFJAL-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 3 hour

    10.1002/anie.200907287 · ORD ord-2e733412453844acb39bfbc6d500a2e2

29. Minisci alkylation: Caffeine + CHF3O2SZn · ORD YSNORGWKORDJSP-UHFFFAOYSA-N → C9H9F3N4O2 · ORD GAQUXLIKHSGSGP-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 12 hour; Atmosphere: air

    10.1038/nature11680 · ORD ord-57e064e40ad34fb19550033d43abbfeb

30. Sulfonamide synthesis: Benzylamine + C8H9ClO4S · ORD RSJSYCZYQNJQPY-UHFFFAOYSA-N → C15H17NO4S · ORD VKKVQTFXBJRYSB-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-30961b140f914d0fb2ad4cc9bdc0bf17

31. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-iodo,4-fluorobenzene → C15H20FNO2 · ORD TZYOXZVGHGCZMZ-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-3f67aa5592fd434d97a577988d3fd241

32. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H8ClF3O · ORD FMKOVXXCOSGLCT-ZCFIWIBFSA-N → C18H17F3O2 · ORD FEKIJYBUZLEDDL-OOPCZODUSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-48cb5430272f43a2b77d809fadf5f623

33. Borylation: C8H11N · ORD JLTDJTHDQAWBAV-UHFFFAOYSA-N → C14H22BNO2 · ORD DGMLJJIUOFKPKB-UHFFFAOYSA-N

    Temperature: 100 °C; Time: 24 hour; Atmosphere: argon

    10.1002/anie.201611536 · ORD ord-092f34ffbc8d4bf2834ae0e8a1b27f27

34. Nickel-catalyzed cross-coupling: Acetophenone + C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N → C18H14O · ORD VQENQLFGWQHXKF-UHFFFAOYSA-N

    Temperature: 120 °C; Time: 24 hour

    10.1002/anie.201403823 · ORD ord-1c0d99144510441a9270b685421f6068

35. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + Propanoic acid → C12H13N · ORD UNCNHFIHYIDOIF-UHFFFAOYSA-N

    Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

    10.1021/acs.orglett.8b02988 · ORD ord-206c372a31ed46d398dfbeb17fdc9eb8

36. Sulfonamide synthesis: Morpholine + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C13H19NO3S · ORD QGOLVCFGOQOJAA-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-44d0cf5c785a45a8b99f02f13945a2f4

37. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 2-bromo,5-trifluoromethylpyridine → C15H19F3N2O2 · ORD SWIVHNNHAFOOGZ-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-42d02699e3324267a38f0c0d31bfe6e4

38. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C10H11Cl · ORD URZAPYFJGQXLKY-SNVBAGLBSA-N → C19H20O · ORD WYNGKTSHDROPME-KQPPXVQYSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-4afab9ea6ff446bd9b32827be38095c1

39. Borylation: C13H16F3NO · ORD MJALYHCWBYHLDF-UHFFFAOYSA-N → C19H27BF3NO3 · ORD RRECHEYWZXAEHZ-UHFFFAOYSA-N + C19H27BF3NO3 · ORD FMFJQILJSXJJER-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 20 hour; Atmosphere: argon

    10.1002/anie.201708967 · ORD ord-03493c8fbc6d4f73b834a599f010615a

40. Nickel-catalyzed cross-coupling: C24H22O4 · ORD YIAQRNNJNMLGTP-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C29H24O2 · ORD DWNFDQJQYNIEGK-UHFFFAOYSA-N

    Temperature: 66 °C; Time: 24 hour

    10.1002/chem.201003731 · ORD ord-01620ebcad10497f8627a651a8b81ac7

41. Minisci alkylation: Quinoline + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C11H7F4N · ORD LJECGMKCSXJXGA-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 18 hour; Atmosphere: air

    10.1021/ja211422g · ORD ord-92c16e39dde241cd821b8b2ebb598238

42. Sulfonamide synthesis: Benzylamine + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C13H12N2O4S · ORD OKABXQCJRCTYLI-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-460799004ab944a2a387bfaf2dda9bb0

43. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-iodo,4-methylbenzene → C16H23NO2 · ORD BHCCYSKURJPWSW-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-42e2098904ab491e9a348d65f0dddb47

44. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C11H13Cl · ORD MUHPMVKOWZJCII-LLVKDONJSA-N → C20H22O · ORD OXDIFILTRWKIMR-HGZMWJMZSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-4d88969608854d6ea6a9cb76966b1d9c

45. Borylation: Benzamide → C13H18BNO3 · ORD NWEMAGLLVQDEKL-UHFFFAOYSA-N + C13H18BNO3 · ORD BPKIPHYWHVOWMS-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 12 hour; Atmosphere: argon

    10.1002/anie.201809929 · ORD ord-8a61495c860141f1a8046698b9543528

46. Nickel-catalyzed cross-coupling: C14H21NO2 · ORD IZNMHGFRJFLYSK-UHFFFAOYSA-N + C13H16Li2Zn · ORD RQQALDKYRKUJIO-UHFFFAOYSA-N → C24H27NO · ORD FJWUYWJUJWSDQT-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 9 hour

    10.1002/chem.201103784 · ORD ord-034b877749b343f996c0536d9d0c2b05

47. Minisci alkylation: C20H26N2O2 · ORD LJOQGZACKSYWCH-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C23H30N2O3 · ORD DPRXNZZTKURJBX-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 0.8 hour; Atmosphere: air

    10.1021/jo9010624 · ORD ord-079d5ee961d349b3860c3cad94f9eab1

48. Sulfonamide synthesis: Glycine + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C9H11NO4S · ORD VDKFCCZUCXYILI-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-5134201167564f99aaefb2c648def79d

49. Decarboxylative sp3–sp2 cross-coupling: Boc-Morph-OH + 1-acetyl-4-bromobenzene → C17H23NO4 · ORD LIHPUINNXBZQBH-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-5a3239d982264f8c8dc20d57d17e3036

50. Electroreductive cross-coupling: C11H13BrO · ORD KWAVEFKPFFCKBQ-XBXARRHUSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C19H22O · ORD LQEGOCGQUWVJJZ-VMSUTVGLSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-6f58b9fc4228408184023447b55ae3a4

51. Borylation: C15H15NO2 · ORD GEFZSLMGZREDTO-UHFFFAOYSA-N → C21H26BNO4 · ORD QRPSPGOTSUZAMP-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 96 hour; Atmosphere: nitrogen

    10.1002/anie.201907366 · ORD ord-07a7ddd270ed4ee294d08bcca20357f0

52. Nickel-catalyzed cross-coupling: C12H12O · ORD GUMOJENFFHZAFP-UHFFFAOYSA-N + C6H5Li · ORD NHKJPPKXDNZFBJ-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 12 hour

    10.1002/chem.201603436 · ORD ord-0b0b961d15984688a7771de90e23d879

53. Minisci alkylation: Caffeine + CH3FO2SZn · ORD HGWRELAVWVPFSN-UHFFFAOYSA-N → C9H11FN4O2 · ORD AXXQFBYOHQLECI-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 18 hour; Atmosphere: air

    10.1038/nature11680 · ORD ord-9cd2aa12f30544689cefbb9bb7b631bb

54. Sulfonamide synthesis: Aniline + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C13H13NO2S · ORD VLVCWODDMDGANW-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-a243e9d11d3547d5b7e98b6d15b58f07

55. Decarboxylative sp3–sp2 cross-coupling: Boc-N-Me-Leu-OH + 1-acetyl-4-bromobenzene → C19H29NO3 · ORD AVBCJQYQGVCRDF-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-660cb87b15dd4f7c815fc992b97bb989

56. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C17H18O · ORD MIKLVVLQKIJPBZ-VFNNOXKTSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-76ac76ddff4041c5b4e05ca3d58f7db5

57. Borylation: C13H14BrNO · ORD TUCSLJFSOTXKRX-UHFFFAOYSA-N → C14H17BBrNO2 · ORD HZJSZZRPDUPDQR-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 16 hour; Atmosphere: nitrogen

    10.1002/anie.201909786 · ORD ord-0f68b60183de4d489ba1fadb5f86de76

58. Nickel-catalyzed cross-coupling: Anisole + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C13H12 · ORD ZZLCFHIKESPLTH-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 4 hour

    10.1002/ejic.201900692 · ORD ord-1cba7c55ed4349058a9992f2b412b7c2

59. Minisci alkylation: C11H8O2 · ORD MJVAVZPDRWSRRC-UHFFFAOYSA-N + Propanoic acid → C13H12O2 · ORD QWIBLPIAYFAQQQ-UHFFFAOYSA-N

    Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

    10.1021/acs.orglett.8b02988 · ORD ord-a62adabc2f494f2985e343f7aaaebc01

60. Sulfonamide synthesis: Benzylamine + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C14H15NO2S · ORD WTHKAJZQYNKTCJ-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-d2c4ec0927a44a2b8b90f7ace120ecf4

61. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 2-bromo,4-methylpyridine → C15H22N2O2 · ORD YZWSKJURJFYISS-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-79badf0360ad46e6abd001d683df2718

62. Electroreductive cross-coupling: C4H6BrCl · ORD WOLCEETZOXGERP-HNQUOIGGSA-N + C9H11ClO · ORD YOANFEVQVLUDDA-UHFFFAOYSA-N → C13H17ClO · ORD BTWBRCWRDHZCON-GQOHGMTASA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-7b0b23336ede44c787ba874780ee3be9

63. Borylation: Tetrahydrofuran → C10H19BO3 · ORD KEBDNHHRQNZXMA-UHFFFAOYSA-N

    Temperature: 100 °C; Time: 48 hour; Atmosphere: argon

    10.1021/acscatal.0c00152 · ORD ord-1b73a405c8194ffc886473eef2273b6c

64. Nickel-catalyzed cross-coupling: C12H13NO2 · ORD KVCYRHCBMVONNS-UHFFFAOYSA-N + C6H15O3P · ORD BLKXLEPPVDUHBY-UHFFFAOYSA-N → C13H18NO3P · ORD RXINMJQMNDSCKD-UHFFFAOYSA-N

    Temperature: 110 °C; Time: 46 hour

    10.1021/acs.joc.6b00289 · ORD ord-011d03874e264f86867f1c58fbd301f2

65. Minisci alkylation: Cyclohexanone + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C7H10F2O · ORD AOXSKWSBHVVGMI-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 18 hour; Atmosphere: air

    10.1021/ja211422g · ORD ord-d51500b03fe841a88e9a1159a0bbb3ff

66. Sulfonamide synthesis: Benzylamine + C8H7ClO3S · ORD FXVDNCRTKXMSEZ-UHFFFAOYSA-N → C15H15NO3S · ORD VWVJYCFXEACLPD-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-da3bc58398004833be4daf633e73715a

67. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-iodo,4-methoxybenzene → C16H23NO3 · ORD ATSPMVQBNBDWRI-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-882b04a893f8431780b44fbe7c6bb751

68. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C8H8ClF · ORD ZWOBTWLZWFIELC-ZCFIWIBFSA-N → C17H17FO · ORD BEUSMKJELSWXAE-OOPCZODUSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-81ca5303d7f14f0884fca3ce0db15f66

69. Borylation: C7H3Cl2N · ORD KUWBYWUSERRVQP-UHFFFAOYSA-N → C13H14BCl2NO2 · ORD USJOSEVEPCTAMO-UHFFFAOYSA-N + C13H14BCl2NO2 · ORD IJUABOWVAKKDPN-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 18 hour; Atmosphere: nitrogen

    10.1021/ja0428309 · ORD ord-502144bb24ec47d5a8090f4ed0dbd46e

70. Nickel-catalyzed cross-coupling: C11H15BO2 · ORD FQMSNYZDFMWLGC-UHFFFAOYSA-N + C11H15NO2 · ORD XOIJDIYJCTXRQR-UHFFFAOYSA-N → Biphenyl

    Temperature: 120 °C; Time: 24 hour

    10.1021/acs.joc.6b01627 · ORD ord-0884f932294246b6854ebe88867c3ab2

71. Minisci alkylation: C8H8N2 · ORD FGYADSCZTQOAFK-UHFFFAOYSA-N + C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N → C16H21N3O2 · ORD QYKQPQSZTOJOLV-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 2 hour; Atmosphere: air

    10.1021/jo9010624 · ORD ord-0810a7b8e5134dada871394b3a94393d

72. Sulfonamide synthesis: Morpholine + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C11H15NO3S · ORD NBTTYMBZXDHFCP-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-fae8732b1f0f4d6a831af0156c37bd51

73. Decarboxylative sp3–sp2 cross-coupling: Boc-Trp(Boc)-OH + 1-acetyl-4-bromobenzene → C28H34N2O5 · ORD FBPSWWHMNFAOHL-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-8c8d5cbe7313457197480b73e68c5e45

74. Electroreductive cross-coupling: C8H8BrNO · ORD GCMADNGHSHZETK-SNAWJCMRSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C16H17NO · ORD HZQPNFYQQHFLGU-XEHSLEBBSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-8261e6378225435c97217152a6c5ff85

75. Borylation: C9H8ClN · ORD WUVWAXJXPRYUME-UHFFFAOYSA-N → C15H19BClNO2 · ORD CZGYEJPYWNMRCD-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 20 hour; Atmosphere: nitrogen

    10.1021/ja0631652 · ORD ord-2c33c866d4e348449996e934f2708a85

76. Nickel-catalyzed cross-coupling: C11H10O · ORD NQMUGNMMFTYOHK-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C17H14 · ORD JTZVTVSSLYYVAM-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 10 hour

    10.1021/acs.organomet.5b00874 · ORD ord-0f2986199da74ae0a302a7b30a9d234c

77. Minisci alkylation: Caffeine + C2H3F3O2SZn · ORD MPPCXQHXDLRDRL-UHFFFAOYSA-N → C10H11F3N4O2 · ORD AHALIRHRLNWEHN-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 18 hour; Atmosphere: air

    10.1038/nature11680 · ORD ord-e2e653bdc1fd49ccb37422bbc4fb7d61

78. Sulfonamide synthesis: C6H6IN · ORD VLVCDUSVTXIWGW-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C13H12INO2S · ORD CLEZIWMPIJOFOG-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-00b28c352e6a453398fad16ac35a55c6

79. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-bromo,4-trifluoromethylbenzene → C16H20F3NO2 · ORD VRTPZKNGIPJWGT-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-91d90a16b6d748dd994d6e66921b1514

80. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H11Cl · ORD WQLQKKZHEUQVBU-MRVPVSSYSA-N → C18H20O · ORD WPRRFMAZEYPQON-LFAOLKIESA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-8b4db80c7c6f4e86a37a02a3fe8dc3f0

81. Borylation: Indole → C14H18BNO2 · ORD QAXZRSICOHKXML-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 4 hour; Atmosphere: nitrogen

    10.1021/ja1006405 · ORD ord-c9153d663e534bab94406784b3ece553

82. Nickel-catalyzed cross-coupling: C15H16O3 · ORD CUFPXYFHDGLCPI-UHFFFAOYSA-N + C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N → C17H14O · ORD HMJIYPQPQDOHRP-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 4 hour

    10.1021/acs.organomet.9b00543 · ORD ord-05d777461d6140119919332b643c18a5

83. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + C6H10O3 · ORD AVPKHOTUOHDTLW-UHFFFAOYSA-N → C15H17NO · ORD QGVHDXNKCPZBIH-UHFFFAOYSA-N

    Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

    10.1021/acs.orglett.8b02988 · ORD ord-029e21a5d69442eea78ff2cd2e29af14

84. Sulfonamide synthesis: C5H13N · ORD IGEIPFLJVCPEKU-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C14H23NO2S · ORD QISAWUNBCUVJIV-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-04df145abead4a48977c3a7e32cc698e

85. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 4-chloro,6-phenylpyrimidine → C19H23N3O2 · ORD TXPDKWUNQGTHHO-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-980f59be0fef4944a93d6d926e7c186a

86. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H11ClO · ORD UIXXSMPGNUPHSA-SSDOTTSWSA-N → C18H20O2 · ORD RVQYHJBCLMQERW-VFNNOXKTSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-8bfa0e57bc21432e90048d6913f56a3f

87. Borylation: C14H6F7NO · ORD RNPQALWWIIZYLA-UHFFFAOYSA-N → C20H17BF7NO3 · ORD QMCZFCGKAVWDHJ-UHFFFAOYSA-N

    Temperature: 80 °C; Time: 12 hour; Atmosphere: air

    10.1021/ja2097095 · ORD ord-023a74e447fe49c990b8868ee7ea5e9c

88. Nickel-catalyzed cross-coupling: C10H20B2O4 · ORD MDNDJMCSXOXBFZ-UHFFFAOYSA-N + Anisole → Biphenyl

    Temperature: 120 °C; Time: 12 hour

    10.1021/acs.orglett.5b03151 · ORD ord-d2fee5942a354e57bd610d982e1dc6a6

89. Minisci alkylation: C13H13N3 · ORD JQSHBVHOMNKWFT-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C14H13F2N3 · ORD XZDZOKMHWBERFG-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 18 hour; Atmosphere: air

    10.1021/ja211422g · ORD ord-09609265281445cc82c1adf5500fe478

90. Sulfonamide synthesis: C9H11N · ORD LBUJPTNKIBCYBY-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C18H21NO2S · ORD YDUJUUVGZIPXJO-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-05d160f1b7da441183b9fa501f445612

91. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 2-trifluoromethyl,5-bromopyridine → C15H19F3N2O2 · ORD WMFBOCLLDDGRND-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-aec9d01590b046a4bee2b2a86f3fd5e0

92. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H9ClO2 · ORD XPBSWFGBJVQTDZ-ZCFIWIBFSA-N → C18H18O3 · ORD WTTJUNJOAWSYHI-OOPCZODUSA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-9073b8b740b64c76bd6d936e46d84fe4

93. Borylation: C11H14BrNO2 · ORD VLGPDTPSKUUHKR-UHFFFAOYSA-N → C17H25BBrNO4 · ORD OMPQXBQRXIONDR-UHFFFAOYSA-N

    Temperature: 50 °C; Time: 22 hour; Atmosphere: nitrogen

    10.1021/ja303443m · ORD ord-0335307c23a84b7ab8ea02c9791ec636

94. Nickel-catalyzed cross-coupling: C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M + C15H17NO · ORD CDUPUVUDMVIGAC-UHFFFAOYSA-N → C21H21N · ORD SMWWZNRJCXJPNB-UHFFFAOYSA-N

    Temperature: 60 °C; Time: 24 hour

    10.1021/acs.orglett.6b02656 · ORD ord-044aae029a9b4c889908f8f3b5c4ff9c

95. Minisci alkylation: C8H9NO2 · ORD MCRPKBUFXAKDKI-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C11H13NO3 · ORD PHTCPCSTKJJVJF-UHFFFAOYSA-N

    Temperature: 40 °C; Time: 1.5 hour; Atmosphere: air

    10.1021/jo9010624 · ORD ord-2658d2fffcce43018f8455223d2c38f6

96. Sulfonamide synthesis: C9H11N · ORD LBUJPTNKIBCYBY-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C16H17NO2S · ORD GFQYTRYDCBOWCV-UHFFFAOYSA-N

    Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

    10.1021/co400012m · ORD ord-07552ce5a98241a68653a51d24d1218e

97. Decarboxylative sp3–sp2 cross-coupling: Tetrahydro-2 furoic acid + 1-acetyl-4-bromobenzene → C12H14O2 · ORD GSLXRVJKAQYAFQ-UHFFFAOYSA-N

    Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

    10.1126/science.1255525 · ORD ord-b1a9540efa8a4ab1b9ae318a0d9c0627

98. Electroreductive cross-coupling: C14H18BBrO2 · ORD GEHSUAZNFIDYOS-MDZDMXLPSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C22H27BO2 · ORD GEFTYJKDEOXQOA-FLVLSHQESA-N

    Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

    10.1021/acscatal.9b01785 · ORD ord-983567cbb5d244cab96293788fe8b9f7

99. Borylation: C7H7Br · ORD WJIFKOVZNJTSGO-UHFFFAOYSA-N → C13H18BBrO2 · ORD ULWOHZNOAMCALR-UHFFFAOYSA-N

    Temperature: 25 °C; Time: 4 hour; Atmosphere: nitrogen

    10.1021/ja400295v · ORD ord-009c2c4f83eb4008ada91b158b502f8f

100. Nickel-catalyzed cross-coupling: C6H5BrMg · ORD ANRQGKOBLBYXFM-UHFFFAOYSA-M + C12H8O · ORD TXCDCPKCNAJMEE-UHFFFAOYSA-N → C18H14O · ORD XXKHDSGLCLCFSC-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 2 hour

     10.1021/acs.orglett.6b03861 · ORD ord-0643c36a41c64e7297bc47e5d6391d12

101. Minisci alkylation: Caffeine + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C11H16N4O2 · ORD KZIRZQRZLZACTP-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-ea7c4b71a086469394a4a7c53223042b

102. Sulfonamide synthesis: H3N · ORD QGZKDVFQNNGYKY-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C7H9NO2S · ORD LMYRWZFENFIFIT-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-2642c201402c40cba165d232e657aa90

103. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 2-methyl,4-bromopyridine → C15H22N2O2 · ORD LNHUDNBUSGWZEJ-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-cbcfac768325414ab1d753c079ee3782

104. Electroreductive cross-coupling: C4H7BrO · ORD HWSVHRDXHIRTMJ-HNQUOIGGSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C12H16O · ORD PXMDPJYSFFSQPG-ZRQQLDRUSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-a1674a7659ec4286a3ba520bab2e5c74

105. Borylation: Pyrazole → C9H15BN2O2 · ORD TVOJIBGZFYMWDT-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 21 hour; Atmosphere: argon

     10.1021/ja412563e · ORD ord-08c8740451b544899305968e6d09fbb2

106. Nickel-catalyzed cross-coupling: C15H16O3 · ORD CUFPXYFHDGLCPI-UHFFFAOYSA-N + C14H23Al · ORD MSZVPIUTCYUSLM-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 24 hour

     10.1021/acscatal.7b01058 · ORD ord-004434c61c3445ce81796e8a4175144e

107. Minisci alkylation: C14H12N2 · ORD IYRGXJIJGHOCFS-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C26H32N2 · ORD YBPJGUUSTABESQ-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-0697834af53f4fe9ac9cd790ae130cb0

108. Sulfonamide synthesis: C7H9NO · ORD BHAAPTBBJKJZER-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C14H15NO3S · ORD GFPBLDMXBCYORT-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-360f0e1373444a2b9571017ab7c7e186

109. Decarboxylative sp3–sp2 cross-coupling: Cbz-Pro-OH + 1-acetyl-4-bromobenzene → C20H21NO3 · ORD MIMQRLRPRGDKSU-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-cf0d04017ede4c8aab8a15119c53e57b

110. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H8ClF3 · ORD CKKMRMKMZIDSDS-ZCFIWIBFSA-N → C18H17F3O · ORD QVEJZLRJMSJAHL-OOPCZODUSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-a405dd8472064079a9c5d05c0b13dd12

111. Borylation: C9H9N · ORD BLRHMMGNCXNXJL-UHFFFAOYSA-N → C15H20BNO2 · ORD KMLZZUZKSQWHKC-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1021/ja500712z · ORD ord-007e4516c96b4fe39eecc394269f1434

112. Nickel-catalyzed cross-coupling: C9H10N2 · ORD WVNMLOGVAVGQIT-UHFFFAOYSA-N + Anisole → C15H14N2 · ORD NWMBNEWCGZPOIT-UHFFFAOYSA-N

     Temperature: 90 °C; Time: 16 hour

     10.1021/acscatal.8b03436 · ORD ord-0c7e154815894fe0af42053252f23b35

113. Minisci alkylation: C8H9NO2 · ORD MCRPKBUFXAKDKI-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C9H9F2NO2 · ORD OYERJNILKIFGKX-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-0ce5d4d8ece8446b9788386cfbf63776

114. Sulfonamide synthesis: C8H9N · ORD LPAGFVYQRIESJQ-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C15H15NO2S · ORD XRAGAKWEPOMNPH-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-3fc4a035731d4d93b8618efd7a838b3b

115. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 2-chloro,5-fluoropyridine → C14H19FN2O2 · ORD OWYODSMUMJHPBC-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-d26b0806d39f47ca8e967a56e8d38fc7

116. Electroreductive cross-coupling: C11H11BrO2 · ORD NPURBARRYADKBT-XBXARRHUSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C19H20O2 · ORD XPKOZEXVZFUORD-DZZUKKPASA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-a663ff34689a412ca6c338620b30a40e

117. Borylation: Indole → C14H18BNO2 · ORD WQPRSRMWYVTUTE-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 4 hour; Atmosphere: argon

     10.1021/jacs.0c05434 · ORD ord-1d47764836bc48998408c231e6f9c3c9

118. Nickel-catalyzed cross-coupling: C11H15NO2 · ORD XOIJDIYJCTXRQR-UHFFFAOYSA-N + C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N → C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N

     Temperature: 130 °C; Time: 24 hour

     10.1021/ja200398c · ORD ord-024c78fdebc9462fb4cb46a732263034

119. Minisci alkylation: C18H13Cl2N3O2 · ORD IUZCVUGIDCZCEQ-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C21H17Cl2N3O3 · ORD OFKZVFIUCMJERD-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 0.75 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-28ee03ebfec6486d9771f5f5dddac929

120. Sulfonamide synthesis: C12H11N · ORD TWBPWBPGNQWFSJ-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C19H17NO2S · ORD VPIDANAIZIMNGX-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-426951e60a664643a083d7159cbb3384

121. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-bromo,4-carboxybenzene → C16H21NO4 · ORD PPLCFZBVANBKEC-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-ded757113ab1450b9af53f6f08563982

122. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C9H11Cl · ORD MZMVVHAHSRJOEO-SECBINFHSA-N → C18H20O · ORD VLNDNZQJJIRSDZ-YHVDPYDOSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-bce9cf32caa04f2d8ca73fcd8dec5a9d

123. Borylation: C6H4Cl2 · ORD RFFLAFLAYFXFSW-UHFFFAOYSA-N → C12H15BCl2O2 · ORD DTAZBCNEXKOLPE-UHFFFAOYSA-N

     Temperature: 85 °C; Time: 20 hour; Atmosphere: argon

     10.1021/jacs.5b02052 · ORD ord-e6314e92965a4736956197783bb8498a

124. Nickel-catalyzed cross-coupling: C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N + C7H5NO · ORD BCMCBBGGLRIHSE-UHFFFAOYSA-N → C17H11NO · ORD XTFVRSDPQJOAQJ-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/ja210249h · ORD ord-057d0433bd0c45f5a220ba504f388a03

125. Minisci alkylation: C8H9NO2 · ORD MCRPKBUFXAKDKI-UHFFFAOYSA-N + CH3FO2SZn · ORD HGWRELAVWVPFSN-UHFFFAOYSA-N → C10H11F2NO2 · ORD CWABMTGQVGRLCK-UHFFFAOYSA-N + C9H10FNO2 · ORD AVDJSYVAJRQUNI-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-02943d791f4d471195f47a5b366e8b27

126. Sulfonamide synthesis: C7H7NO2 · ORD RWZYAGGXGHYGMB-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C14H13NO4S · ORD ADALGBTXGIISDM-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-4850fd9d6cc64028b1dfe1bd7213d16d

127. Decarboxylative sp3–sp2 cross-coupling: Boc-Pro-OH + 1-iodo,4-chlorobenzene → C15H20ClNO2 · ORD MLNBPUVXUSNQNC-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-ebcb8d7d8b2e42568e4b9900c4530bd6

128. Electroreductive cross-coupling: C9H6BrN · ORD VYWMRUNSZWVTKD-AATRIKPKSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C17H15N · ORD VMAKVZPOZMYOOJ-NPQIQWPPSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-d31a21739b314cc7afcc8d2349e75056

129. Borylation: C6H4Br2 · ORD SWJPEBQEEAHIGZ-UHFFFAOYSA-N → C12H15BBr2O2 · ORD YAZONGAJMOABEV-UHFFFAOYSA-N

     Temperature: 100 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1021/jacs.5b05252 · ORD ord-066c508c5a254808b5bb566fd4b02a47

130. Nickel-catalyzed cross-coupling: C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N + Carbon dioxide → C11H8O2 · ORD UOBYKYZJUGYBDK-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 48 hour

     10.1021/ja410883p · ORD ord-0fdb504bed264b54a8549cb1ca7e4ee0

131. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + C7H10O2 · ORD VUSWCWPCANWBFG-UHFFFAOYSA-N → C16H17N · ORD MLCXOMIZSWRBNA-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-0bb460b52de7453b84457ecce845d517

132. Sulfonamide synthesis: C8H9N · ORD LPAGFVYQRIESJQ-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C17H19NO2S · ORD GNGNIJOTWKGGJV-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-5602ee001aee4e92a35919e5399bb3d5

133. Decarboxylative sp3–sp2 cross-coupling: Boc-Val-OH + 1-acetyl-4-bromobenzene → C17H25NO3 · ORD XBJXCCZXNCYYQD-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-fb9150450d964b1e8515a67a635523f7

134. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C8H8Cl2 · ORD NOCHRVHWICTPLG-ZCFIWIBFSA-N → C17H17ClO · ORD QXMZPOSSUIERCG-OOPCZODUSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-d6b9dd0540384aabb43de1a705566c05

135. Borylation: C26H42N2O4Si · ORD ZNSZNVYIQLMXSG-UHFFFAOYSA-N → C32H53BN2O6Si · ORD WQYMWNHTXBROSP-UHFFFAOYSA-N + C32H53BN2O6Si · ORD NWFGWSSGLFLESF-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: argon

     10.1021/jacs.5b07154 · ORD ord-1a7798d251034c978b5f41b596d603bd

136. Nickel-catalyzed cross-coupling: C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N + C12H27BO2Si · ORD IUQZZPMFYLUYJJ-UHFFFAOYSA-N → C16H22Si · ORD IFSRZMLTNKGPIF-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 2 hour

     10.1021/ja412107b · ORD ord-04f9b8bd7c1241548bf7d58f4d10942b

137. Minisci alkylation: C7H5NS2 · ORD YXIWHUQXZSMYRE-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C8H5F2NS2 · ORD XYUPZERKMMCICQ-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-1a22e1193ad948cb95e32e804572836c

138. Sulfonamide synthesis: C7H9NO · ORD BHAAPTBBJKJZER-UHFFFAOYSA-N + C8H7ClO3S · ORD FXVDNCRTKXMSEZ-UHFFFAOYSA-N → C15H15NO4S · ORD BJHWCUFAXSXPNZ-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-64b2625cf0d0437d98111a403df2197f

139. Decarboxylative sp3–sp2 cross-coupling: C16H21NO6 · ORD FWMXCVVHFCFTTA-UHFFFAOYSA-N + 1-acetyl-4-bromobenzene → C23H27NO5 · ORD GGURUVAUAKTNNN-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-0b453c3805b0490c9fffb6fb51128e7a

140. Electroreductive cross-coupling: C10H17Br · ORD FLMHWDCHCOMUPL-JARNTUPDSA-N + C9H11ClO · ORD YOANFEVQVLUDDA-UHFFFAOYSA-N → C19H28O · ORD AZIFVEFTPXTRDO-JGJWRRPTSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-de1335c72de6418cbe18f8beb8912b7a

141. Borylation: Benzaldehyde → C13H17BO3 · ORD SLJMPQLPRHIAOM-UHFFFAOYSA-N

     Temperature: 90 °C; Time: 12 hour; Atmosphere: nitrogen

     10.1021/jacs.5b11683 · ORD ord-c3bc362270de46efa26dac41e95f14aa

142. Nickel-catalyzed cross-coupling: C26H30O2 · ORD LGAUQWNLQJNCTM-UHFFFAOYSA-N + C5H9NO · ORD HNHVTXYLRVGMHD-UHFFFAOYSA-N → C15H17NO · ORD IKCJNZVSLPKXLB-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour

     10.1021/ja5029793 · ORD ord-082252729bf6471d99cda2e19eb547d5

143. Minisci alkylation: C9H8N2O · ORD GESPRUVYTLDFDD-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C11H10N2O2 · ORD CQMFUXWOJZIWIE-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 1 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-3b08d7848aae4d6da08ad8bfcd983910

144. Sulfonamide synthesis: C3H7N · ORD HTJDQJBWANPRPF-UHFFFAOYSA-N + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C9H10N2O4S · ORD SFXOKDPLGLHGIX-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-683c4052a0684aa1a660247c1152bf80

145. Decarboxylative sp3–sp2 cross-coupling: C10H19NO4S · ORD IMUSLIHRIYOHEV-UHFFFAOYSA-N + 1-acetyl-4-bromobenzene → C17H25NO3S · ORD CHQFTAJQTIAGJY-UHFFFAOYSA-N

     Temperature: 23 °C; Time: 72 hour; Atmosphere: argon

     10.1126/science.1255525 · ORD ord-803fd11e1f5044ef8085cc2c65adbc15

146. Electroreductive cross-coupling: C7H7BrN2O · ORD AJFRQQYCGGSSSE-NSCUHMNNSA-N + C8H9Cl · ORD GTLWADFFABIGAE-UHFFFAOYSA-N → C15H16N2O · ORD UUTCIGMPHFZCFD-BCPZQOPPSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-f329a2f4290c42fa85d2c5a14e0d4667

147. Borylation: m-Xylene → C14H21BO2 · ORD XWCNEQGQJTWRHX-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 43 hour; Atmosphere: nitrogen

     10.1021/jacs.6b06144 · ORD ord-4287abdd324f400681da3e5ae539b609

148. Nickel-catalyzed cross-coupling: C12H10O3 · ORD KOSWEOFSNRRAQH-UHFFFAOYSA-N + C18H15B3O3 · ORD VOXXGUAZBWSUSS-UHFFFAOYSA-N → C16H12O · ORD PZOXFBPKKGTQDZ-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 12 hour

     10.1021/ja8056503 · ORD ord-01f8176700a74753bb53316d1105a3fc

149. Minisci alkylation: C5H5ClN2O · ORD XBJLKXOOHLLTPG-UHFFFAOYSA-N + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C8H11ClN2O · ORD XMFCQZOTUWTDIO-UHFFFAOYSA-N + C8H11ClN2O · ORD ADWXIDAIVDMFOM-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-0589f71f95eb4300a6f0870d4c0a9aa9

150. Sulfonamide synthesis: C7H7NO2 · ORD RWZYAGGXGHYGMB-UHFFFAOYSA-N + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C13H10N2O6S · ORD MWXPPZARWSMLCS-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-6a159be3b3874798b538af3b44c8a7be

151. Electroreductive cross-coupling: C9H9BrO · ORD MNSBHZNBVJAJND-VOTSOKGWSA-N + C14H13Cl · ORD UVROAJFELBNMRA-CQSZACIVSA-N → C23H22O · ORD HLVKPJKUQXUAHO-OWSFEGEDSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-f6b32bf8799e4e04a818357730f2c6e4

152. Borylation: C7H7FO · ORD MFJNOXOAIFNSBX-UHFFFAOYSA-N → C13H18BFO3 · ORD PYGFGOBGKWJERN-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1021/jacs.6b13346 · ORD ord-04d6f2c7c1514ea986686e87526ce250

153. Nickel-catalyzed cross-coupling: C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N + C12H16O2 · ORD WFGQAOWBQYCYEX-UHFFFAOYSA-N → C14H14O · ORD GNYJFZNIMOMCCF-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 24 hour

     10.1021/ja806244b · ORD ord-109cb258f51a489e838aa1ae9a60fa1a

154. Minisci alkylation: C10H6O2 · ORD FRASJONUBLZVQX-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C16H16O2 · ORD LBXMBBATNWKPGI-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-158c75a2f3e24c69b1dad8c16ca66eac

155. Sulfonamide synthesis: C6H6IN · ORD VLVCDUSVTXIWGW-UHFFFAOYSA-N + C8H7ClO3S · ORD FXVDNCRTKXMSEZ-UHFFFAOYSA-N → C14H12INO3S · ORD MDALVSOGCTVJDX-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-7103389eb5f4408998792648c7cead6c

156. Electroreductive cross-coupling: C9H9Br · ORD VDQOXWRCEPPGRE-VOTSOKGWSA-N + C9H11ClO · ORD YOANFEVQVLUDDA-UHFFFAOYSA-N → C18H20O · ORD GNDCRGUZIRSBLP-RZXPCSSPSA-N

     Temperature: 0 °C; Time: 3.25 hour; Atmosphere: argon

     10.1021/acscatal.9b01785 · ORD ord-fb838f91ab174120bb816d633fa2e6c2

157. Borylation: 4-Methylphenol → C13H19BO3 · ORD QUYCGOSWQMOXCJ-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1021/jacs.7b02232 · ORD ord-7e7df91f5c16474cbf653dc44bbbf6e2

158. Nickel-catalyzed cross-coupling: C6H5BrMg · ORD ANRQGKOBLBYXFM-UHFFFAOYSA-M + C12H17NO2 · ORD HEAYNANJBNIHRA-UHFFFAOYSA-N → C13H12 · ORD ZZLCFHIKESPLTH-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 1 hour

     10.1021/ja903091g · ORD ord-1de389a422104d5e855c71f5a6c3628e

159. Minisci alkylation: C20H26N2O2 · ORD LJOQGZACKSYWCH-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C22H25F5N2O2 · ORD YCRCAUBDBAHXON-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-228a58906ec043d9a9d51f0a53134781

160. Sulfonamide synthesis: C9H13N · ORD YKOLZVXSPGIIBJ-UHFFFAOYSA-N + C8H9ClO4S · ORD RSJSYCZYQNJQPY-UHFFFAOYSA-N → C17H21NO4S · ORD CNEIAJSSQCAMBV-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-77844ff3f64843739339d0d7f7c6e5d4

161. Borylation: Indole → C14H18BNO2 · ORD IAQBURSQTCOSBP-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 12 hour; Atmosphere: nitrogen

     10.1021/jacs.7b04490 · ORD ord-e2052b834d4f47a8bce5bc1268dbf810

162. Nickel-catalyzed cross-coupling: C15H17NO2 · ORD PCEIRTKGPDXWOT-UHFFFAOYSA-N + C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N → C17H14O · ORD SOKALMMKJGUKGK-UHFFFAOYSA-N

     Temperature: 130 °C; Time: 24 hour

     10.1021/ja906477r · ORD ord-08de509cf85746a59811aca6ee4c016f

163. Minisci alkylation: C6H8N2O2 · ORD HKQOBAGKDBSVEQ-UHFFFAOYSA-N + C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N → C14H21N3O4 · ORD MHXAKZBKGCDOCO-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 1 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-454464b52369433a8964eca6dbfa5e8b

164. Sulfonamide synthesis: C9H13N · ORD YKOLZVXSPGIIBJ-UHFFFAOYSA-N + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C15H16N2O4S · ORD IAQSCMHNTDDHMB-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-78a192d608b64bc2bfe32f0854c579a5

165. Borylation: C5H7N · ORD OXHNLMTVIGZXSG-UHFFFAOYSA-N → C11H18BNO2 · ORD OEQQEXKRORJZPR-UHFFFAOYSA-N + C11H18BNO2 · ORD SYAMJGBBLFTQTK-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 2 hour; Atmosphere: nitrogen

     10.1021/jacs.7b08143 · ORD ord-17454c9359b344d689e48e8a67a3b3b9

166. Nickel-catalyzed cross-coupling: C19H21NO2 · ORD SACUBPAPXZNVAP-CCEZHUSRSA-N + C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N → C20H16 · ORD CBJPRTGKMYOVJO-FOCLMDBBSA-N

     Temperature: 150 °C; Time: 10 hour

     10.1021/ja907700e · ORD ord-039696dd0ae74ba58dd823308df27790

167. Minisci alkylation: C13H18N4O3 · ORD BYPFEZZEUUWMEJ-UHFFFAOYSA-N + CH3FO2SZn · ORD HGWRELAVWVPFSN-UHFFFAOYSA-N → C14H19FN4O3 · ORD XNXNAGUOJJAOBM-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-0ee895cc6b304408a98aafaa9be5173d

168. Sulfonamide synthesis: C12H15NO2 · ORD VVCLBQFBKZQOAF-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C21H25NO4S · ORD WQZWTYRPZOFJPP-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-8bc54c6029fd40429fc5c05da891f8e6

169. Borylation: C12H15N · ORD DZFWNZJKBJOGFQ-UHFFFAOYSA-N → C18H26BNO2 · ORD BXNYIZZTFZOUAA-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1021/jacs.9b08920 · ORD ord-84938907c6d04c5f8d69938d452761f6

170. Nickel-catalyzed cross-coupling: C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N + C12H17BO2 · ORD ZSPBWRPQSPRISS-UHFFFAOYSA-N → C17H14 · ORD ZXXGUXICWKNYJD-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/jacs.7b04279 · ORD ord-255c106b131b48cc862010cf2e7262a3

171. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + Tetrahydro-2 furoic acid → C14H15NO · ORD QDXNYKYOKLVDRS-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-16e63faae9924ff9989bc4a7c2b532b1

172. Sulfonamide synthesis: C7H7NO2 · ORD RWZYAGGXGHYGMB-UHFFFAOYSA-N + C8H9ClO4S · ORD RSJSYCZYQNJQPY-UHFFFAOYSA-N → C15H15NO6S · ORD VQBNWHIIZMCLDS-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-967ac60e6bb843d7b9d6a50e7ea93962

173. Borylation: C19H29O2P · ORD YCZKCFRODVOYJS-UHFFFAOYSA-N → C25H40BO4P · ORD WPGGMTJJIAWJKM-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour; Atmosphere: argon

     10.1038/nchem.2322 · ORD ord-012064b8316844249cac7c9126c4a796

174. Nickel-catalyzed cross-coupling: C13H19NO4 · ORD DXTZKQVUXKNHJA-UHFFFAOYSA-N + C6H5ClMg · ORD GQONLASZRVFGHI-UHFFFAOYSA-M → C14H14O2 · ORD JRRIIYFCKLVGAP-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour

     10.1021/jo00041a004 · ORD ord-0109b10a4ed940e291bd07f7daaf5d24

175. Minisci alkylation: C7H7NO · ORD WMQUKDQWMMOHSA-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C8H7F2NO · ORD TYLZKBGNHNAPDG-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-24043f9eb4064b3b8242f778d5cc6992

176. Sulfonamide synthesis: C6H6IN · ORD VLVCDUSVTXIWGW-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C15H16INO2S · ORD MTLDEIMAFZWTNB-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-aaa2d6dcba144711a7e3a8582de8f279

177. Borylation: C8H7ClO · ORD ZDOYHCIRUPHUHN-UHFFFAOYSA-N → C14H18BClO3 · ORD OJZIJXVVLUQHKL-UHFFFAOYSA-N + C14H18BClO3 · ORD URNQTFVMOQZYIA-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1039/c2sc20776a · ORD ord-18a75699f8fc40179e3bebc6eaa44775

178. Nickel-catalyzed cross-coupling: C15H17NO2 · ORD SPFHTFNBTUNIJY-UHFFFAOYSA-N + C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

     Temperature: 180 °C; Time: 10 minute

     10.1021/jo1024464 · ORD ord-0e6cf4da4d164e44b1e52425ea75de77

179. Minisci alkylation: C11H12N2O3 · ORD ZRYWDTDJBHKYNL-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C14H16N2O4 · ORD PGOPIGZGFMUHTP-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 1.5 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-47040b4dc9d846d3bba53e0f90a4fd4c

180. Sulfonamide synthesis: C4H9NO2 · ORD NTNZTEQNFHNYBC-UHFFFAOYSA-N + C6H4ClNO4S · ORD JXRGUPLJCCDGKG-UHFFFAOYSA-N → C10H12N2O6S · ORD WFYWPPPBHSWSJM-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-bd879f30d24f4d42b175fe559e3c9ce5

181. Borylation: Dodecane → C18H37BO2 · ORD WHOMEQHZQLKAPC-UHFFFAOYSA-N + C24H48B2O4 · ORD UERUPHTVHREEJD-UHFFFAOYSA-N

     Temperature: 100 °C; Time: 20 hour; Atmosphere: nitrogen

     10.1126/science.aba6146 · ORD ord-627c2f97e4324eeeb624db68fca1e291

182. Nickel-catalyzed cross-coupling: C12H13N3O4 · ORD KQYQLFOENDMYBP-UHFFFAOYSA-N + C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N → C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 24 hour

     10.1021/jo4005537 · ORD ord-06ab83805d854ff1bef29b835f2ea0c0

183. Minisci alkylation: C7H9NO · ORD SZYIVZGXCXFXDN-UHFFFAOYSA-N + CH3FO2SZn · ORD HGWRELAVWVPFSN-UHFFFAOYSA-N → C8H10FNO · ORD BWSCQZHIHKXLQC-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-14f7293c96c0497d9d07c9e2751515c0

184. Sulfonamide synthesis: C5H14N2 · ORD IUNMPGNGSSIWFP-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C12H20N2O2S · ORD MFLRGXNDNKRSKU-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-be98f79220f8485aaa48ed9e41c171ae

185. Borylation: C20H25NO · ORD LNOFXEZDSDQSJI-UHFFFAOYSA-N → C26H36BNO3 · ORD QBWRGSJVZTWTRB-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 48 hour

     10.1126/science.abc8320 · ORD ord-5632a72a1a8c4a5d9651e07af2f5b01d

186. Nickel-catalyzed cross-coupling: C15H16O2 · ORD LQSGTVGOLFWRJY-UHFFFAOYSA-N + C5H4BF3KN · ORD SLPOSOZRTRIRQS-UHFFFAOYSA-N → C15H11N · ORD HBUWLNOJQAZUQZ-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 4 hour

     10.1021/ol101592r · ORD ord-0613dec247ec478fb6967c3abee06913

187. Minisci alkylation: C8H6N2 · ORD LFSXCDWNBUNEEM-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C20H26N2 · ORD BCNMFTDXCHQCSQ-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-1e74701e5eec41f8a7529e0e7d587095

188. Sulfonamide synthesis: C7H9NO · ORD BHAAPTBBJKJZER-UHFFFAOYSA-N + C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N → C16H19NO3S · ORD SZRCZRBFSIPIHK-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-c2e5e7fa7a224532a21ec3ae2bd99098

189. Borylation: C16H13NO · ORD VTMISZOFKPHDIB-UHFFFAOYSA-N → C22H24BNO3 · ORD OMEIICZUICOOQK-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 12 hour; Atmosphere: argon

     10.1002/anie.201104544 · ORD ord-05be27b392b147bd8a072d6a6d75c559

190. Nickel-catalyzed cross-coupling: C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N + C12H17BO2 · ORD ZSPBWRPQSPRISS-UHFFFAOYSA-N → C19H16 · ORD XNYPQVNKEFUPST-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/ol502583h · ORD ord-19b4b91f970c4c6f804e7f7922b0dc85

191. Minisci alkylation: C9H8O2 · ORD MSTDXOZUKAQDRL-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C10H8F2O2 · ORD DUQTWCCORQSHPT-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-27c354e5e2514ff69ab34fe5da58c644

192. Sulfonamide synthesis: C5H13N · ORD IGEIPFLJVCPEKU-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C12H19NO2S · ORD ODMWZCBRHGGIGM-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-d72f32ee6c78415fbceb5c568b3e8d20

193. Borylation: C8H15NO · ORD OWXPHZLYDIDNFZ-UHFFFAOYSA-N → C14H26BNO3 · ORD MGDVJAOPVFEGKV-UHFFFAOYSA-N

     Temperature: 70 °C; Time: 18 hour; Atmosphere: nitrogen

     10.1002/anie.201409186 · ORD ord-38cadda2a33648a9ad5bbd9f93ac95f2

194. Nickel-catalyzed cross-coupling: C12H12N2O2 · ORD HGFFUYIDPDPZEP-UHFFFAOYSA-N + C18H15B3O3 · ORD VOXXGUAZBWSUSS-UHFFFAOYSA-N → C15H11N · ORD QAQUJJBBUGVGMO-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 16 hour

     10.1021/ol9029534 · ORD ord-48c5360b326744d3b8bb865956232f05

195. Minisci alkylation: C20H26N2O2 · ORD LJOQGZACKSYWCH-UHFFFAOYSA-N + C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N → C28H39N3O4 · ORD RBYUYDNLIGPELY-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 0.75 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-65b545b2ce404f6ab07d9ff218ea13d7

196. Sulfonamide synthesis: C7H9N · ORD AFBPFSWMIHJQDM-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C14H15NO2S · ORD HEFFCQILGLLHQC-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-e9be4dfdfbf445aaaec5e20a86047cb9

197. Borylation: C13H12F7NO · ORD VGLQEIXJBXPKJV-UHFFFAOYSA-N → C19H23BF7NO3 · ORD HMJMZIMRTJPXGG-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 15 hour; Atmosphere: oxygen

     10.1002/anie.201509996 · ORD ord-058279c7f35f4dc0ba18c02ccededa40

198. Nickel-catalyzed cross-coupling: Anisole + CH3BrMg · ORD AVFUHBJCUUTGCD-UHFFFAOYSA-M → Toluene

     Temperature: 110 °C; Time: 20 minute

     10.1039/B718998B · ORD ord-04266f052710482dbac40bec22ba5ed2

199. Minisci alkylation: C9H8N2 · ORD ALHUXMDEZNLFTA-UHFFFAOYSA-N + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C12H14N2 · ORD LRDBSRNPJQJWMO-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-21755b54d05841a9a2afe4f7dbf742e4

200. Sulfonamide synthesis: C4H9NO2 · ORD NTNZTEQNFHNYBC-UHFFFAOYSA-N + C8H7ClO3S · ORD FXVDNCRTKXMSEZ-UHFFFAOYSA-N → C12H15NO5S · ORD BOPYUOAOFOPROX-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-f0631987000e4cb8baa4e5711ee63af6

201. Borylation: C8H7NS · ORD IHTFSBAUENZVAX-UHFFFAOYSA-N → C14H18BNO2S · ORD OISKEFUGLPBVNA-UHFFFAOYSA-N

     Temperature: 55 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1002/anie.201610041 · ORD ord-0dc5c76273764473a9c47b34bf982241

202. Nickel-catalyzed cross-coupling: C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N + C19H18O2 · ORD NNLUDDFJYFYFSY-UHFFFAOYSA-N → C20H14 · ORD LUBXLGUQZVKOFP-UHFFFAOYSA-N

     Temperature: 100 °C; Time: 6 hour

     10.1039/C3CC46663A · ORD ord-09443c57f0df4fc2858fb24c20b40acf

203. Minisci alkylation: C8H6N2 · ORD JWVCLYRUEFBMGU-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C14H16N2 · ORD PCBIYRDQGSBDTM-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-217de7f77ff243ab860ea18d9b4a7e48

204. Sulfonamide synthesis: C3H7N · ORD HTJDQJBWANPRPF-UHFFFAOYSA-N + C7H7ClO2S · ORD YYROPELSRYBVMQ-UHFFFAOYSA-N → C10H13NO2S · ORD PFGWZABBMVYDBP-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-fad05a16500b48ffba64bb9c56303c57

205. Borylation: C18H29NSi · ORD SLORZAYPAQKLCZ-UHFFFAOYSA-N → C24H40BNO2Si · ORD COEPRFQMETYEEE-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 72 hour; Atmosphere: argon

     10.1002/anie.201611536 · ORD ord-147ffd4a44b54602a4cf9c7f7939ea78

206. Nickel-catalyzed cross-coupling: C9H11NO2 · ORD MYOHNZJKOAODMX-UHFFFAOYSA-N + Oxazole → C9H7NO · ORD RQCBPOPQTLHDFC-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 36 hour

     10.1039/C5SC02942B · ORD ord-39ba5825f8c9418ca6544ed804cf9675

207. Minisci alkylation: C6H4N2 · ORD GPHQHTOMRSGBNZ-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C7H4F2N2 · ORD MHIVNBZOWUQBSC-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-2d6510a99676427baa7b832568afd7d7

208. Sulfonamide synthesis: C5H11NO2 · ORD KVQGGLZHHFGHPU-UHFFFAOYSA-N + C8H9ClO4S · ORD RSJSYCZYQNJQPY-UHFFFAOYSA-N → C13H19NO6S · ORD QFPCWUOVKGIKCR-UHFFFAOYSA-N

     Temperature: 25 °C; Pressure: 100 psi; Time: 20 minute

     10.1021/co400012m · ORD ord-fd989edc957840599955fbf9a02cabb0

209. Borylation: C10H9F4NO · ORD BALKMMYOCJAUEO-UHFFFAOYSA-N → C16H20BF4NO3 · ORD XJXZEUWDGPLNHG-UHFFFAOYSA-N + C16H20BF4NO3 · ORD NLECBTQVPKXXQZ-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 20 hour; Atmosphere: argon

     10.1002/anie.201708967 · ORD ord-061a7ea6016048c1bd19d5920926e678

210. Nickel-catalyzed cross-coupling: C12H10O3 · ORD LUSSNKSMQDHEQS-UHFFFAOYSA-N + C7H6BF3O2 · ORD ALMFIOZYDASRRC-UHFFFAOYSA-N → C17H11F3 · ORD WAMZBPUDXGSDGC-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 48 hour

     10.1246/cl.2011.913 · ORD ord-0aa88fcd592b4f94bcb9f0b2df7f42ef

211. Minisci alkylation: C9H8N2 · ORD ALHUXMDEZNLFTA-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C12H12N2O · ORD JBQUQIFVKBRVGK-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 1.5 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-692777e0346141d795b86ad587ec5cde

212. Borylation: C15H23NO · ORD RYGJQVQEGCQNHM-UHFFFAOYSA-N → C21H34BNO3 · ORD ZFPYVEOWHUBIFH-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 12 hour; Atmosphere: argon

     10.1002/anie.201809929 · ORD ord-03012762915d4ccdbd8b6fdfaf5ceb80

213. Nickel-catalyzed cross-coupling: C13H22O3Si · ORD FGLFSDHJENOLAP-UHFFFAOYSA-N + C12H12N2O2 · ORD WHKWXMFRFOHXGZ-UHFFFAOYSA-N → C16H13N · ORD MCPPOQZFTOUOIH-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1002/adsc.201600590 · ORD ord-050cb7371a644988b21aa864caea7b2f

214. Minisci alkylation: C7H9NO · ORD SZYIVZGXCXFXDN-UHFFFAOYSA-N + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C10H15NO · ORD HIKHXWYYBQSGHG-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-2863c94d553844fc9089c6880b147885

215. Borylation: C15H12F3NO · ORD MVMBCPQNHHXPIH-UHFFFAOYSA-N → C21H23BF3NO3 · ORD WNSNMCNLWZNKKE-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 96 hour; Atmosphere: nitrogen

     10.1002/anie.201907366 · ORD ord-0b96b962765f4cca8835ec98c058a5a4

216. Nickel-catalyzed cross-coupling: C11H14O · ORD SUFDFKRJYKNTFH-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C17H18 · ORD QEZMSFVMIVYNEK-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 6 hour

     10.1002/anie.200453765 · ORD ord-018f5c03a7b3407ab0d75bfd81901b86

217. Minisci alkylation: C11H8O2 · ORD MJVAVZPDRWSRRC-UHFFFAOYSA-N + C6H8O2 · ORD VPFMEXRVUOPYRG-UHFFFAOYSA-N → C16H14O2 · ORD MFVCYBQHUQRSKE-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-272966bc256247ff818a05a9e994525b

218. Borylation: C13H15NO · ORD DTRSVKLNWUNCQE-UHFFFAOYSA-N → C19H26BNO3 · ORD DEWYSULLSQVBJV-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1002/anie.201909786 · ORD ord-164577140edc436c99d9264e80008fb8

219. Nickel-catalyzed cross-coupling: C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N + C24H20BNa · ORD HFSRCEJMTLMDLI-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 12 hour

     10.1002/anie.200801447 · ORD ord-0cd7e8f7a9634764b59c4576b06b65ed

220. Minisci alkylation: C13H18N4O3 · ORD BYPFEZZEUUWMEJ-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C14H18F2N4O3 · ORD ZWYQGSGYQXGVPG-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-42c53d95efa4494796212f716a9695f9

221. Borylation: 1-bromo,3-fluoro,4-cyanobenzene → C13H14BBrFNO2 · ORD CVVZEHHIEWRAAA-UHFFFAOYSA-N + C13H14BBrFNO2 · ORD FAGYMAOSACMWSQ-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 9 hour; Atmosphere: nitrogen

     10.1021/ja0428309 · ORD ord-5e7f3eae47f147d3b723e00940fd0e6d

222. Nickel-catalyzed cross-coupling: Morpholine + C18H19NO2 · ORD UEMZMPSQXAPWJF-UHFFFAOYSA-N → C17H18N2O · ORD CJVDUSGCZFBVOY-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 3 hour

     10.1002/anie.200907287 · ORD ord-2ecd8e0afe144385989bb49f57d53867

223. Minisci alkylation: C18H13Cl2N3O2 · ORD IUZCVUGIDCZCEQ-UHFFFAOYSA-N + C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N → C26H26Cl2N4O4 · ORD QTHUSZKQIGNCRB-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 1.1 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-6ae06cd6fdb442dfae1c1f5a96560381

224. Borylation: C11H15NSi · ORD ISPRGDKNJYQULU-UHFFFAOYSA-N → C17H26BNO2Si · ORD DYUKBTITVHRVLS-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 1 hour; Atmosphere: nitrogen

     10.1021/ja0631652 · ORD ord-4c9fab8ee46943cda11e836695e3f680

225. Nickel-catalyzed cross-coupling: Acetophenone + C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N → C46H34O2 · ORD IJBRHQFOMHRPKL-UHFFFAOYSA-N

     Temperature: 150 °C; Time: 24 hour

     10.1002/anie.201403823 · ORD ord-5289a19bd47e46c488a82e8cb9e65ea1

226. Minisci alkylation: C7H9NO · ORD SZYIVZGXCXFXDN-UHFFFAOYSA-N + C2H3F3O2SZn · ORD MPPCXQHXDLRDRL-UHFFFAOYSA-N → C11H11F6NO · ORD OQOQWUPYYSCXHA-UHFFFAOYSA-N + C9H10F3NO · ORD BVDVZRPMMGBGFS-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-29364894e28f452d9266c81bcb9df4c7

227. Borylation: C12H9N · ORD UJOBWOGCFQCDNV-UHFFFAOYSA-N → C18H20BNO2 · ORD LJHNBACDLZYSIS-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 0 hour; Atmosphere: nitrogen

     10.1021/ja1006405 · ORD ord-091aff459b28440595d0d1de880ae278

228. Nickel-catalyzed cross-coupling: C13H16OSi · ORD YDJRVQVCDFEELI-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C17H14 · ORD JTZVTVSSLYYVAM-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 16 hour

     10.1002/chem.201003731 · ORD ord-06ca5144ef644b2e86f8b2ac5f6eef93

229. Minisci alkylation: C8H6N2O · ORD QMNUDYFKZYBWQX-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C14H16N2O · ORD MEWDLKFIQDINLZ-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 24 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-3c7e8185485c4bf58074ca45e7482d26

230. Borylation: C15H8F7NO · ORD ZVYDSGJHUBKURU-UHFFFAOYSA-N → C21H19BF7NO3 · ORD ZTMRGEGYBUKPCF-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: air

     10.1021/ja2097095 · ORD ord-07dc922d06514dcda29ba37887e079f1

231. Nickel-catalyzed cross-coupling: C19H28O2Si · ORD RMHPAOHIVIOGON-UHFFFAOYSA-N + C9H14Li2Zn · ORD UEBHSGDLLXKCML-UHFFFAOYSA-N → C24H30OSi · ORD MMBHGMSMFHDRBB-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 9 hour

     10.1002/chem.201103784 · ORD ord-06024163c8884fb49ab27a1eee76a484

232. Minisci alkylation: C9H8N2 · ORD ALHUXMDEZNLFTA-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C10H8F2N2 · ORD SCIPVGZJINFOMN-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-43a2ef8de4f94c2fa24550810614f612

233. Borylation: C11H15NO3 · ORD YRQMBQUMJFVZLF-UHFFFAOYSA-N → C17H26BNO5 · ORD NTRVTYZUMZBMMS-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 12 hour; Atmosphere: nitrogen

     10.1021/ja303443m · ORD ord-1139608af0de453f8fc0d7e140ea28b2

234. Nickel-catalyzed cross-coupling: C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N + CH3Li · ORD DVSDBMFJEQPWNO-UHFFFAOYSA-N → C11H10 · ORD QIMMUPPBPVKWKM-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 12 hour

     10.1002/chem.201603436 · ORD ord-1091a8dda4354acea3af21347b87e078

235. Minisci alkylation: C10H9N · ORD FVVXWRGARUACNW-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C13H13NO · ORD HWZCJZPMSNGQDS-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 0.8 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-6c6bc5ae0eb34da6b5c49cf73fe096b5

236. Borylation: C8H10O2 · ORD DPZNOMCNRMUKPS-UHFFFAOYSA-N → C14H21BO4 · ORD CZYHRTIJLUONKY-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 8 hour; Atmosphere: nitrogen

     10.1021/ja400295v · ORD ord-014658cd6f544a5ba56a0368f81a1014

237. Nickel-catalyzed cross-coupling: C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N + C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M → C17H14 · ORD ZXXGUXICWKNYJD-UHFFFAOYSA-N

     Temperature: 100 °C; Time: 4 hour

     10.1002/ejic.201900692 · ORD ord-04106cfe99ce472b80165fd576f9c918

238. Minisci alkylation: C5H3N3 · ORD IIHQNAXFIODVDU-UHFFFAOYSA-N + C2H3F3O2SZn · ORD MPPCXQHXDLRDRL-UHFFFAOYSA-N → C7H4F3N3 · ORD NCGWDYPCPLMFKO-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-2a9c2a07d2b64fddb079be1c83a3335a

239. Borylation: Pyrimidine → C10H15BN2O2 · ORD WSRGGSAGSUEJKQ-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 25 hour; Atmosphere: argon

     10.1021/ja412563e · ORD ord-78b58e0b90c04617962d5f11f826e8b8

240. Nickel-catalyzed cross-coupling: C11H14O2 · ORD PUXKSJCSTXMIKR-UHFFFAOYSA-N + C6H15O3P · ORD BLKXLEPPVDUHBY-UHFFFAOYSA-N → C12H19O3P · ORD CTLLAZAHTUAAGH-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 24 hour

     10.1021/acs.joc.6b00289 · ORD ord-12194793d7634dcea98141ecc1874bbb

241. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + C6H10O2 · ORD JBDSSBMEKXHSJF-UHFFFAOYSA-N → C15H17N · ORD BOKUGJPCJBRYHH-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-428e40fdef8b44f3aa57867685e1f306

242. Borylation: C6H7N · ORD BSKHPKMHTQYZBB-UHFFFAOYSA-N → C12H18BNO2 · ORD MBTULFIFECUURA-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1021/ja500712z · ORD ord-743548bea2e0400c88996cd6a1e0177c

243. Nickel-catalyzed cross-coupling: C11H15BO2 · ORD FQMSNYZDFMWLGC-UHFFFAOYSA-N + C15H17NO2 · ORD SPFHTFNBTUNIJY-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 24 hour

     10.1021/acs.joc.6b01627 · ORD ord-03eadff305c04d7ab2658aaff2a09769

244. Minisci alkylation: C8H9NO3 · ORD JIRJAOSTLIQOCY-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C9H9F2NO3 · ORD LEGXWKCPNDRHJB-UHFFFAOYSA-N + C9H9F2NO3 · ORD MJDUAMVWDJGGSU-UHFFFAOYSA-N + C9H9F2NO3 · ORD ZDAFXCRCSXFAHW-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-46ec5ff5d8a0412a95b56b4da9ce56fd

245. Borylation: C8H6FN · ORD YYFFEPUCAKVRJX-UHFFFAOYSA-N → C14H17BFNO2 · ORD WBMUILOQZNJVBY-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 4 hour; Atmosphere: argon

     10.1021/jacs.0c05434 · ORD ord-170551bb44624a89b40eae81aa3c6036

246. Nickel-catalyzed cross-coupling: C8H10O · ORD CHLICZRVGGXEOD-UHFFFAOYSA-N + C7H7BrMg · ORD DVXDIGKNJYSMFM-UHFFFAOYSA-M → C14H14 · ORD SHMKKPZGLDISGT-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 10 hour

     10.1021/acs.organomet.5b00874 · ORD ord-a484fec79b294998b62270bf4067c250

247. Minisci alkylation: C22H24ClFN4O3 · ORD XGALLCVXEZPNRQ-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C25H28ClFN4O4 · ORD FJVNPBRXSMUTPY-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 0.5 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-875738a3ebdc47d99b5dec0d61c0e057

248. Borylation: C8H7BrO · ORD JYAQYXOVOHJRCS-UHFFFAOYSA-N → C14H18BBrO3 · ORD HAUZUTGHWBQWTM-UHFFFAOYSA-N

     Temperature: 150 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1021/jacs.5b05252 · ORD ord-0df2332035b54748b7ae7ffafed6e61e

249. Nickel-catalyzed cross-coupling: C15H16O3 · ORD CUFPXYFHDGLCPI-UHFFFAOYSA-N + C8H11BO2 · ORD ZXDTWWZIHJEZOG-UHFFFAOYSA-N → C18H16 · ORD DYJVADCPNYBVBL-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 4 hour

     10.1021/acs.organomet.9b00543 · ORD ord-0a40b71b52044d37810c759df392c98f

250. Minisci alkylation: C5H3ClN4 · ORD ZKBQDFAWXLTYKS-UHFFFAOYSA-N + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C9H9ClF2N4 · ORD ZSMLAOUEFJIOQY-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-313eecc3ba344c5abbe0fa0e5c45126a

251. Borylation: C23H33NSi · ORD BGSQHMSMBCFURC-UHFFFAOYSA-N → C29H44BNO2Si · ORD IVUCTLXQIKOKRL-UHFFFAOYSA-N + C29H44BNO2Si · ORD NEHYVXORCLZNEC-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour; Atmosphere: argon

     10.1021/jacs.5b07154 · ORD ord-34826959d1bc4c97898ab86dc41580e6

252. Nickel-catalyzed cross-coupling: C10H20B2O4 · ORD MDNDJMCSXOXBFZ-UHFFFAOYSA-N + C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N → C20H14 · ORD MSBVBOUOMVTWKE-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/acs.orglett.5b03151 · ORD ord-02afca7e5afe4cd9b61c30ab2653d118

253. Minisci alkylation: C7H9N · ORD OISVCGZHLKNMSJ-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C13H19N · ORD XXCIZUNJCWEMES-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-432ffa6753a745788e43706fe162c294

254. Borylation: C8H8O · ORD OVWYEQOVUDKZNU-UHFFFAOYSA-N → C14H19BO3 · ORD CGHQBKWBUKSEBB-UHFFFAOYSA-N

     Temperature: 90 °C; Time: 12 hour; Atmosphere: nitrogen

     10.1021/jacs.5b11683 · ORD ord-02e529dadf584eb2ad65978440415c1a

255. Nickel-catalyzed cross-coupling: C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N + C7H7ClMg · ORD YBPFQOFSPMWGKA-UHFFFAOYSA-M → C17H14 · ORD ZXXGUXICWKNYJD-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 24 hour

     10.1021/acs.orglett.6b02656 · ORD ord-04b206652b6b4c0f8bfdbb816bad507e

256. Minisci alkylation: C2H3N3S · ORD QUKGLNCXGVWCJX-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C3H3F2N3S · ORD NBGMELMIAOKZSD-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-49f9caf458e4464ab9e52809e2b0ee0f

257. Borylation: Toluene → C13H19BO2 · ORD XDKYCZBGHPGKEP-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 43 hour; Atmosphere: nitrogen

     10.1021/jacs.6b06144 · ORD ord-569e06f9c9914e7fa68d69361f4213d5

258. Nickel-catalyzed cross-coupling: C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M + C12H8O · ORD TXCDCPKCNAJMEE-UHFFFAOYSA-N → C19H16O · ORD IJLOFQAUVYZHDI-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 2 hour

     10.1021/acs.orglett.6b03861 · ORD ord-1e998cbfb7ea4c9dbcf670fc03e7f8ed

259. Minisci alkylation: C10H9N · ORD MUDSDYNRBDKLGK-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C13H13NO · ORD YVLUMSNFYVKNMF-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 0.75 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-89c7d517418648fd92734995b148b41b

260. Borylation: C9H9FO2 · ORD SMMIKBXLEWTSJD-UHFFFAOYSA-N → C15H20BFO4 · ORD ZXSGWPHDXQZIAF-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1021/jacs.6b13346 · ORD ord-08ddf5ec2e6a40b3acf143be724c313b

261. Nickel-catalyzed cross-coupling: C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N + C14H23Al · ORD MSZVPIUTCYUSLM-UHFFFAOYSA-N → C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 24 hour

     10.1021/acscatal.7b01058 · ORD ord-03df13d366f0409b8f71eea96497bb84

262. Minisci alkylation: C7H8ClNO2 · ORD WKJRYVOTVRPAFN-UHFFFAOYSA-N + CHF3O2SZn · ORD YSNORGWKORDJSP-UHFFFAOYSA-N → C8H6F3NO2 · ORD RLWKWLRQVHPBDQ-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 24 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-316b8ce895954fe5a7b1712c65a9a0f2

263. Borylation: Phenol → C12H17BO3 · ORD VLROJECCXBBKPZ-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 2 hour; Atmosphere: nitrogen

     10.1021/jacs.7b02232 · ORD ord-c2b5ef0483ed4d5182be5f4568e9da87

264. Nickel-catalyzed cross-coupling: C17H18N2 · ORD BYBKSBRSHGTGPE-UHFFFAOYSA-N + Anisole → C23H22N2 · ORD OQLOMRFORXNIBV-UHFFFAOYSA-N

     Temperature: 90 °C; Time: 16 hour

     10.1021/acscatal.8b03436 · ORD ord-1d733776d5164df29623e7ebbbedfb20

265. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C16H19N · ORD FUDPYOPZEFDRFK-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-52de714f0ca342bbb41f6b45117859e5

266. Borylation: C9H8BrFO2 · ORD ODFAIHQRCRQZGM-UHFFFAOYSA-N → C15H19BBrFO4 · ORD GTWTUFZYPOZBKG-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 12 hour; Atmosphere: nitrogen

     10.1021/jacs.7b04490 · ORD ord-0f930c207abc4c73a4f92506d0df4d13

267. Nickel-catalyzed cross-coupling: C15H17NO2 · ORD PCEIRTKGPDXWOT-UHFFFAOYSA-N + C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N → C16H12 · ORD IYDMICQAKLQHLA-UHFFFAOYSA-N

     Temperature: 150 °C; Time: 12.5 hour

     10.1021/ja200398c · ORD ord-0258ea754df147698be2b7409a47f743

268. Minisci alkylation: C7H5NOS · ORD FLFWJIBUZQARMD-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C8H5F2NOS · ORD NLOMLGNIZUHTKC-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-5444292b4a7f4c8f844d3212362a14c7

269. Borylation: C6H6O2S · ORD GKWLILHTTGWKLQ-UHFFFAOYSA-N → C12H17BO4S · ORD HRLHWIMNIQOHRF-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 6 hour; Atmosphere: nitrogen

     10.1021/jacs.7b08143 · ORD ord-40214ff4ce0d4d03aa7760f498a76e0b

270. Nickel-catalyzed cross-coupling: C13H13NO2 · ORD HWXRSDPITDEWLJ-UHFFFAOYSA-N + C7H5NO · ORD BCMCBBGGLRIHSE-UHFFFAOYSA-N → C17H11NO · ORD XTFVRSDPQJOAQJ-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/ja210249h · ORD ord-2137ed5ec6d448e6bee999d6b18ed4ae

271. Minisci alkylation: C8H8N2 · ORD FGYADSCZTQOAFK-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C11H12N2O · ORD UMZINEBODJUZMR-UHFFFAOYSA-N

     Temperature: 60 °C; Time: 3 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-98133d0b8a69408ba939cadb7f0b7452

272. Borylation: C19H30ClNO · ORD YLXJZILDBRLBMT-UHFFFAOYSA-N → C25H41BClNO3 · ORD PHYXVXPMWYMQNW-UHFFFAOYSA-N + C25H41BClNO3 · ORD CSRGKUUWZMFRCJ-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour; Atmosphere: argon

     10.1038/nchem.2322 · ORD ord-0337d2f5f87247f795d864efbda2616b

273. Nickel-catalyzed cross-coupling: C20H18O2 · ORD LNWIRRLKHOIPNW-UHFFFAOYSA-N + Carbon dioxide → C11H8O2 · ORD UOBYKYZJUGYBDK-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 48 hour

     10.1021/ja410883p · ORD ord-17949ba5b33d4087905ce479d590285b

274. Minisci alkylation: C7H6BrNO · ORD LDBPZEQZCOUYFT-UHFFFAOYSA-N + C3H8O2SZn · ORD BIJCVIGQFTXRRN-UHFFFAOYSA-N → C10H12BrNO · ORD PURPYXPHCFCVKT-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 18 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-326f55e501a44a0c9280dadd1dc989c1

275. Borylation: C9H10O2 · ORD WVWZECQNFWFVFW-UHFFFAOYSA-N → C15H21BO4 · ORD GUHFNSOJOCZHQO-UHFFFAOYSA-N + C15H21BO4 · ORD WBHBKJFHYGIUQU-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 16 hour; Atmosphere: nitrogen

     10.1039/c2sc20776a · ORD ord-19c4d9b183614cef9fce523033f6b00a

276. Nickel-catalyzed cross-coupling: C12H10O2 · ORD RJNPPEUAJCEUPV-UHFFFAOYSA-N + C12H27BO2Si · ORD IUQZZPMFYLUYJJ-UHFFFAOYSA-N → C16H22Si · ORD IFSRZMLTNKGPIF-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 15 hour

     10.1021/ja412107b · ORD ord-12a3199a40b24ed49275e11166976d83

277. Minisci alkylation: C11H8O3 · ORD OBGBGHKYJAOXRR-UHFFFAOYSA-N + C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N → C17H18O3 · ORD IGIKWUIKEWSXSO-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-54db0ab06d604438ab433c420bd8b211

278. Borylation: C11H23N · ORD BBYSGWAYRRMWOW-UHFFFAOYSA-N → C17H34BNO2 · ORD OIKGNJTWNWQBLW-UHFFFAOYSA-N

     Temperature: 100 °C; Time: 20 hour; Atmosphere: nitrogen

     10.1126/science.aba6146 · ORD ord-04774ceac0e04925b547f57d94f715cc

279. Nickel-catalyzed cross-coupling: C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N + C5H9NO · ORD HNHVTXYLRVGMHD-UHFFFAOYSA-N → C15H17NO · ORD IKCJNZVSLPKXLB-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour

     10.1021/ja5029793 · ORD ord-0a3434e911fb4cbeac55d059776f16bf

280. Minisci alkylation: C9H14N2 · ORD PSINWXIDJYEXLO-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C10H14F2N2 · ORD JTFUEYIQOYEPLR-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-59c85b5dc7cf48cd8b72f063f8cb688a

281. Borylation: C12H17NO · ORD JBTCHCWUNMZNEO-UHFFFAOYSA-N → C18H28BNO3 · ORD DFTJEGFAFTVYCU-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 48 hour

     10.1126/science.abc8320 · ORD ord-594d2240eda641bfad1cb4da007f380a

282. Nickel-catalyzed cross-coupling: C12H10O2 · ORD VGKONPUVOVVNSU-UHFFFAOYSA-N + C18H15B3O3 · ORD VOXXGUAZBWSUSS-UHFFFAOYSA-N → C16H12 · ORD IYDMICQAKLQHLA-UHFFFAOYSA-N

     Temperature: 110 °C; Time: 12 hour

     10.1021/ja8056503 · ORD ord-0268d1eb59dd46559b409ea52be9dc6b

283. Minisci alkylation: C11H11NO · ORD MBVGYFIYXWVPQY-UHFFFAOYSA-N + C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N → C14H15NO2 · ORD DNJBYNNGIMGAAV-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 0.75 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-982651e5df54413da5924287e4d47a9b

284. Borylation: C21H15N · ORD IYOWVDAWQANKHJ-UHFFFAOYSA-N → C27H26BNO2 · ORD DAFGOMSOCOTYCA-UHFFFAOYSA-N

     Temperature: 50 °C; Time: 7 hour; Atmosphere: argon

     10.1002/anie.201104544 · ORD ord-0837ae1efc6d4b7fb5b2a67ee40ac839

285. Nickel-catalyzed cross-coupling: C15H16O2 · ORD LQSGTVGOLFWRJY-UHFFFAOYSA-N + C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N → C16H12 · ORD IYDMICQAKLQHLA-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 24 hour

     10.1021/ja806244b · ORD ord-17eca6b4bfc64331adb72797b51efd2a

286. Minisci alkylation: C7H6BrNO · ORD LDBPZEQZCOUYFT-UHFFFAOYSA-N + CHF3O2SZn · ORD YSNORGWKORDJSP-UHFFFAOYSA-N → C8H5BrF3NO · ORD SDRBNYNQUIOTBF-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 24 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-532695b758824fa9b5b376507ef24a88

287. Borylation: C11H21NO · ORD GEVZQEQTRSXXME-UHFFFAOYSA-N → C17H32BNO3 · ORD TYWYGKRFXLHFNU-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 18 hour; Atmosphere: nitrogen

     10.1002/anie.201409186 · ORD ord-84a1619a2aaa485aa3d6761aec50cd2f

288. Nickel-catalyzed cross-coupling: C6H5BrMg · ORD ANRQGKOBLBYXFM-UHFFFAOYSA-M + C16H24N2O4 · ORD ABCUTBFYSXRGFI-UHFFFAOYSA-N → C17H19NO2 · ORD ZTMCLHQCGHSJBU-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 7 hour

     10.1021/ja903091g · ORD ord-1f80fc91351044169de00370335b01e3

289. Minisci alkylation: C11H8O2 · ORD MJVAVZPDRWSRRC-UHFFFAOYSA-N + C7H12O4 · ORD WLJVNTCWHIRURA-UHFFFAOYSA-N → C17H18O4 · ORD ICGRXHWXPCXIKM-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 16 hour; Atmosphere: argon

     10.1021/acs.orglett.8b02988 · ORD ord-556b821e18394c20bb6e5b604264b391

290. Borylation: C22H22F7NO2 · ORD FCQNPSRIBVPIPR-UHFFFAOYSA-N → C28H33BF7NO4 · ORD FTTRWBOUOUIEMU-UHFFFAOYSA-N

     Temperature: 80 °C; Time: 15 hour; Atmosphere: oxygen

     10.1002/anie.201509996 · ORD ord-092edf7c2a86407abc9c399fec1a8813

291. Nickel-catalyzed cross-coupling: C15H17NO2 · ORD SPFHTFNBTUNIJY-UHFFFAOYSA-N + C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N → C17H14O · ORD HMJIYPQPQDOHRP-UHFFFAOYSA-N

     Temperature: 130 °C; Time: 24 hour

     10.1021/ja906477r · ORD ord-1414f5b1b9ca484da4b1a34bfe10383e

292. Minisci alkylation: C10H14N2 · ORD SNICXCGAKADSCV-UHFFFAOYSA-N + CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N → C11H14F2N2 · ORD HSIDOGLSIYBTDY-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 18 hour; Atmosphere: air

     10.1021/ja211422g · ORD ord-5aa44087f05943f089d00cf46aa8a1b4

293. Borylation: C10H14S · ORD JXOLTWIALSFLTO-UHFFFAOYSA-N → C16H25BO2S · ORD BGYQKSOBPYKRRK-UHFFFAOYSA-N

     Temperature: 55 °C; Time: 24 hour; Atmosphere: nitrogen

     10.1002/anie.201610041 · ORD ord-12ec8b3ea5864f8da66ba4813f640c50

294. Nickel-catalyzed cross-coupling: C11H14FNO2 · ORD JHISYNVCHBCMCS-UHFFFAOYSA-N + C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N → C13H11FO · ORD LOZCDFKRNKCRLO-UHFFFAOYSA-N

     Temperature: 150 °C; Time: 10 hour

     10.1021/ja907700e · ORD ord-08bbe84851964903a314a77062bc3020

295. Minisci alkylation: C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N + C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N → C18H22N2O2 · ORD UZRFQQVRHMBUIL-UHFFFAOYSA-N

     Temperature: 40 °C; Time: 1 hour; Atmosphere: air

     10.1021/jo9010624 · ORD ord-98336091cd12456389bc47ef2d32dae4

296. Borylation: C8H10ClN · ORD CHHCCYVOJBBCIY-UHFFFAOYSA-N → C14H21BClNO2 · ORD RXMYNVPSIWXIRO-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 48 hour; Atmosphere: argon

     10.1002/anie.201611536 · ORD ord-154b9e18939b49648eff4bcd0e35713b

297. Nickel-catalyzed cross-coupling: C11H15BO2 · ORD FQMSNYZDFMWLGC-UHFFFAOYSA-N + C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N → C18H14 · ORD XJKSTNDFUHDPQJ-UHFFFAOYSA-N

     Temperature: 120 °C; Time: 12 hour

     10.1021/jacs.7b04279 · ORD ord-50558bf0af724e9795914b366e8ae49b

298. Minisci alkylation: C5H5ClN2O · ORD XBJLKXOOHLLTPG-UHFFFAOYSA-N + CHF3O2SZn · ORD YSNORGWKORDJSP-UHFFFAOYSA-N → C6H4ClF3N2O · ORD LITNBBZLCLZEMR-UHFFFAOYSA-N + C8H5BrF3NO · ORD LJIMXIWOZUHRLI-UHFFFAOYSA-N

     Temperature: 25 °C; Time: 24 hour; Atmosphere: air

     10.1038/nature11680 · ORD ord-598a113173594a4f87467083f8ff9a33

Teaching reaction reference index / 教学反应参考目录

• Chlorination: Alcohols → Chloroalkanes

  醇可转化为氯代烷，为后续取代反应引入更易离去的基团。

• Chlorination with thionyl chloride: Alcohols → Chloroalkanes

  氯化亚砜将醇转化为氯代烷，同时生成二氧化硫和氯化氢。

• Bromination: Alcohols → Bromoalkanes

  在溴化物和酸的作用下，醇转化为溴代烷。

• Iodination: Alcohols → Iodoalkanes

  在碘和红磷的作用下，醇转化为碘代烷。

• Hydrochlorination: Alkenes → Chloroalkanes

  氯化氢在烯烃双键两端加成，可生成氯代烷。

• Hydrobromination: Alkenes → Bromoalkanes

  溴化氢在烯烃双键两端加成，可生成溴代烷。

• Hydroiodination: Alkenes → Iodoalkanes

  碘化氢在烯烃双键两端加成，可生成碘代烷。

• Hydrolysis: Chloroalkanes → Alcohols

  氢氧根可取代 C-Cl 中的氯，形成醇。

• Cyanation: Chloroalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Cyanation: Bromoalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Cyanation: Iodoalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Amination: Chloroalkanes → Amines

  氨取代氯，形成伯胺；过量氨可限制进一步烷基化。

• Amination: Bromoalkanes → Amines

  氨取代溴，形成伯胺；过量氨可限制进一步烷基化。

• Amination: Iodoalkanes → Amines

  氨取代碘，形成伯胺；过量氨可限制进一步烷基化。

• Elimination: Chloroalkanes → Alkenes

  碱促进的消去反应脱去 HCl，生成烯烃。

• Hydrolysis: Bromoalkanes → Alcohols

  氢氧根可取代 C-Br 中的溴，形成醇。

• Hydrolysis: Iodoalkanes → Alcohols

  氢氧根可取代 C-I 中的碘，形成醇。

• Elimination: Bromoalkanes → Alkenes

  碱促进的消去反应脱去 HBr，生成烯烃。

• Elimination: Iodoalkanes → Alkenes

  碱促进的消去反应脱去 HI，生成烯烃。

• Cyanohydrin formation: Aldehydes → Hydroxynitriles

  氰根与醛加成生成羟基腈，构成从羰基化合物出发、增加一个碳原子的路线。

• Cyanohydrin formation: Ketones → Hydroxynitriles

  氰根与酮加成生成羟基腈，为有机反应网络增加另一条羰基路线。

• Iodoform reaction: Methyl ketones → Triiodomethane 个产物

  碱性碘溶液将甲基酮转化为黄色三碘甲烷和减少一个碳原子的羧酸盐。

• Iodoform reaction: Ethanal → Triiodomethane 个产物

  乙醛在碱性碘溶液中发生碘仿反应，生成三碘甲烷和甲酸盐。

• Iodoform reaction: Ethanol → Triiodomethane 个产物

  乙醇被碱性碘溶液氧化并断裂，生成三碘甲烷和甲酸盐。

• Iodoform reaction: Methyl secondary alcohols → Triiodomethane 个产物

  含 CH3CH(OH)- 结构的仲醇先氧化为甲基酮，再断裂生成三碘甲烷和减少一个碳原子的羧酸盐。

• Oxidation: Alcohols → Aldehydes

  伯醇经受控氧化可生成醛。

• Oxidation: Alcohols → Ketones

  仲醇氧化生成酮。

• Oxidation: Alcohols → Carboxylic acids

  伯醇充分氧化生成羧酸。

• Controlled oxidation: Primary alcohols → Aldehydes

  伯醇经受控氧化可生成醛。

• Complete oxidation: Primary alcohols → Carboxylic acids

  伯醇充分氧化生成羧酸。

• Oxidation: Secondary alcohols → Ketones

  仲醇氧化生成酮。

• Reduction: Aldehydes → Primary alcohols

  醛还原生成伯醇。

• Reduction: Ketones → Secondary alcohols

  酮还原生成仲醇。

• Reduction: Carboxylic acids → Primary alcohols

  羧酸还原生成伯醇。

• Oxidation: Aldehydes → Carboxylic acids

  醛氧化生成羧酸。

• Alkylation: Amines → Quaternary ammonium compounds

  胺可进一步烷基化，形成永久带正电的季铵基团，用于抗菌与离子交换材料。

• Surface immobilization: Quaternary ammonium compounds → Antibacterial coatings

  固定在表面的季铵基团被研究用于接触型抗菌涂层。

• Hydrolysis: Nitriles → Carboxylic acids

  腈可水解为羧酸；此处将原先合并的腈到酰胺路线拆分为单步官能团转化。

• Reduction: Nitriles → Amines

  腈可还原为伯胺，将胺的制备与后续酰胺或材料化学分开呈现。

• Activation for amide formation: Carboxylic acids → Amide chemistry

  羧酸或经活化的羧酸衍生物可用于形成酰胺键。

• Polycondensation: Amide chemistry → Polyamide-related materials

  重复形成酰胺键，可制得尼龙类纤维和工程塑料等聚酰胺相关材料。

• Free radical chlorination: Alkanes → Chloroalkanes

  光化学氯化可将烷烃转化为氯代烷。

• Free radical bromination: Alkanes → Bromoalkanes

  光化学溴化可将烷烃转化为溴代烷。

• Cracking: Alkanes → Alkenes

  热裂解或催化裂解将长链烷烃转化为较短的分子，其中包括烯烃。

• Hydrogenation: Alkenes → Alkanes

  氢化将烯烃还原为烷烃。

• Halogen addition: Alkenes → Dihalogenoalkanes

  溴加成将烯烃转化为邻二溴代烷。

• Dihydroxylation: Alkenes → Diols

  冷的稀高锰酸盐溶液可将烯烃氧化为邻二醇，避免较强条件下的氧化断裂。

• Addition polymerisation: Alkenes → Addition polymers

  烯烃可通过链式加成形成加聚物。

• Hydration: Alkenes → Alcohols

  催化水合将烯烃转化为醇。

• Dehydration: Alcohols → Alkenes

  脱水将醇转化为烯烃。

• Esterification: Carboxylic acids → Esters

  羧酸与醇反应形成酯。

• Esterification co reactant: Alcohols → Esters

  醇与羧酸结合形成酯。

• Hydrolysis: Esters → Carboxylic acids

  酯经水解重新生成羧酸产物。

• Hydrolysis co product: Esters → Alcohols

  酯水解也会重新生成相应的醇。

• Chlorination: Carboxylic acids → Acyl chlorides

  PCl5 将羧酸转化为酰氯。

• Chlorination with thionyl chloride: Carboxylic acids → Acyl chlorides

  氯化亚砜将羧酸转化为酰氯，同时生成二氧化硫和氯化氢。

• Hydrolysis: Acyl chlorides → Carboxylic acids

  水使酰氯水解为羧酸，同时释放氯化氢。

• Acylation: Acyl chlorides → Esters

  醇发生酰化，将酰氯转化为酯。

• Acylation: Acyl chlorides → Amides

  氨发生酰化，将酰氯转化为酰胺。

• Acylation: Acyl chlorides → N-substituted amides

  胺发生酰化，将酰氯转化为 N-取代酰胺。

• Acylation co reactant: Amines → N-substituted amides

  胺被酰氯酰化，形成 N-取代酰胺。

• Grignard formation: Chloroalkanes → Grignard reagents

  氯代烷可在无水乙醚中与镁反应，形成格氏试剂。

• Grignard formation: Bromoalkanes → Grignard reagents

  溴代烷可在无水乙醚中与镁反应，形成格氏试剂。

• Grignard formation: Iodoalkanes → Grignard reagents

  碘代烷可在无水乙醚中与镁反应，形成格氏试剂。

• Carbonyl addition: Grignard reagents → Primary alcohols

  格氏试剂与甲醛加成，经后处理得到伯醇。

• Carbonyl addition: Grignard reagents → Secondary alcohols

  格氏试剂与醛加成，经后处理得到仲醇。

• Carbonyl addition: Grignard reagents → Tertiary alcohols

  格氏试剂与酮加成，经后处理得到叔醇。

• Carboxylation: Grignard reagents → Carboxylic acids

  格氏羧化经酸性后处理得到羧酸。

• Grignard addition co reactant: Methanal → Primary alcohols

  甲醛与格氏试剂反应，经酸性后处理得到伯醇。

• Grignard addition co reactant: Aldehydes → Secondary alcohols

  醛与格氏试剂反应，经酸性后处理得到仲醇。

• Grignard addition co reactant: Ketones → Tertiary alcohols

  酮与格氏试剂反应，经酸性后处理得到叔醇。

• Grignard carboxylation co reactant: Carbon dioxide → Carboxylic acids

  二氧化碳与格氏试剂反应，经酸性后处理得到羧酸。

• Charged polymer network: Quaternary ammonium compounds → Ion-exchange materials

  季铵基团可在离子交换树脂和膜中形成固定的阳离子位点。

• Complete combustion: Alkanes → Carbon dioxide

  烷烃在过量氧气中完全燃烧，生成二氧化碳和水。

• Complete combustion: Alcohols → Carbon dioxide

  醇在过量氧气中完全燃烧，生成二氧化碳和水。

• Combustion: Benzene → Carbon dioxide

  苯燃烧生成二氧化碳和水，通常呈有烟火焰。

• Salt formation: Carboxylic acids → Carboxylate salts

  羧酸与碱、碳酸盐及活泼金属反应，形成羧酸盐。

• Bromination: Benzene → Halogenoarenes

  苯在卤素载体催化剂作用下发生溴化，形成溴苯。

• Nitration: Benzene → Nitroarenes

  苯与浓硝酸、浓硫酸发生硝化，形成硝基苯。

• Friedel Crafts alkylation: Benzene → Alkylarenes

  傅克烷基化在苯环上引入烷基。

• Friedel Crafts acylation: Benzene → Acylbenzenes

  傅克酰基化在苯环上引入酰基。

• Bromination: Phenols → Bromophenols

  苯酚使溴水褪色，并形成浅色的 2,4,6-三溴苯酚沉淀。

• Reduction: Nitroarenes → Aromatic amines

  硝基芳烃经锡和盐酸还原，再用碱处理，得到芳香胺。

• Weak base equilibrium: Amines → Aqueous alkylammonium ions

  胺在水中是弱碱，可形成烷基铵离子和氢氧根离子。

• Salt formation: Amines → Amine salts

  胺与酸反应，形成烷基铵盐。

• Copper(II) complex formation: Amines → Copper-amine complexes

  胺与水溶液中的铜(II)离子反应，胺过量时形成深蓝色配合物。

• Peptide formation: Amino acids → Peptides and proteins

  Controlled amino-acid coupling forms peptide bonds; the displayed equation is a net relationship rather than a complete experimental procedure.

• Peptide hydrolysis: Peptides and proteins → Amino acids

  肽键可通过与盐酸水溶液长时间加热而水解；若需游离氨基酸，还须进行后处理。

• Polyester formation: Dicarboxylic acids → Polyesters

  二羧酸与二醇缩合，形成聚酯。

• Polyester formation co reactant: Diols → Polyesters

  二醇与二羧酸缩合，形成聚酯。

• Polyamide formation: Dicarboxylic acids → Polyamide-related materials

  二羧酸与二胺缩合，形成聚酰胺。

• Polyamide formation co reactant: Diamines → Polyamide-related materials

  二胺与二羧酸缩合，形成聚酰胺。

• Epoxidation: Alkenes → Epoxides

  过氧酸以协同步骤将氧转移到烯烃双键两端，形成两个 C-O 键并断开 C=C 的 π 键。两个键从同一面形成，使烯烃取代基的相对立体关系在环氧产物中保留。

• Epoxide hydrolysis: Epoxides → Diols

  质子化使有张力的环更易受到水的进攻。背面进攻断开一个 C-O 键，质子转移后在相邻碳上形成羟基；当环几何结构允许区分时，两者呈反式加成关系。

• Anhydride hydrolysis: Acid anhydrides → Carboxylic acids

  水进攻酸酐羰基；四面体中间体消除时断开酰基与氧的连接。质子转移后生成羧酸；混合酸酐会产生两种不同的酸。

• Anhydride alcoholysis: Acid anhydrides → Esters

  醇氧进攻酸酐羰基，四面体中间体随后排出羧酸根。质子转移生成酯和羧酸；其中一个酰基片段转移到醇上。

• Anhydride ammonolysis: Acid anhydrides → Amides

  氨进攻酸酐羰基，形成四面体中间体。羧酸根离去及质子转移后生成酰胺；过量氨还会使伴生的羧酸转化为羧酸铵。

• Oxidation: Propanal → Propanoic acid

  丙醛氧化为丙酸。

• Partial oxidation: Ethanol → Ethanal

  乙醇氧化为乙醛。

• Oxidation: Ethanol → Ethanoic acid

  乙醇氧化为乙酸。

• Partial oxidation: Propan-1-ol → Propanal

  1-丙醇氧化为丙醛。

• Oxidation: Propan-1-ol → Propanoic acid

  1-丙醇氧化为丙酸。

• Oxidation: Propan-2-ol → Propanone

  2-丙醇氧化为丙酮。

• Oxidation: Ethanal → Ethanoic acid

  乙醛氧化为乙酸。

• Reduction: Ethanal → Ethanol

  乙醛还原为乙醇。

• Reduction: Propanal → Propan-1-ol

  丙醛还原为 1-丙醇。

• Reduction: Propanone → Propan-2-ol

  丙酮还原为 2-丙醇。

• Esterification: Ethanoic acid → Ethyl acetate

  乙酸与乙醇可逆反应，形成乙酸乙酯和水。

• Esterification: Ethanol → Ethyl acetate

  乙酸与乙醇可逆反应，形成乙酸乙酯和水。

• Acid hydrolysis: Ethyl acetate → Ethanoic acid

  乙酸乙酯与水可逆反应，形成乙酸和乙醇。

• Acid hydrolysis: Ethyl acetate → Ethanol

  乙酸乙酯与水可逆反应，形成乙酸和乙醇。

• Hydration: Ethene → Ethanol

  乙烯通过水合生成乙醇。

• Dehydration: Ethanol → Ethene

  乙醇通过脱水生成乙烯。

• Hydration: Propene → Propan-2-ol

  丙烯通过水合生成 2-丙醇。

• Dehydration: Cyclohexanol → Cyclohexene

  环己醇通过脱水生成环己烯。

• Ring hydrogenation: Benzene → Cyclohexane

  苯通过芳香环氢化生成环己烷。

• Ring hydrogenation: Toluene → Methylcyclohexane

  甲苯通过芳香环氢化生成甲基环己烷。

• Nitration: Benzene → Nitrobenzene

  苯通过硝化生成硝基苯。

• Nitro reduction and basification: Nitrobenzene → Aniline

  硝基苯的硝基经还原，再进行碱化处理，生成苯胺。

• Side chain oxidation: Toluene → Benzoic acid

  甲苯通过侧链氧化生成苯甲酸。

• Partial hydrogenation: But-2-yne → cis-But-2-ene

  炔烃吸附于催化剂表面，从同一面接受两个氢原子。这种顺式加成生成顺-2-丁烯；活性受抑制的 Lindlar 催化剂有助于限制产物继续还原为丁烷。

• Dissolving metal reduction: But-2-yne → trans-But-2-ene

  连续的电子转移和质子化使三键转化为双键。中间体依次变化时有利于形成位阻较小的排列，最终得到反-2-丁烯；这一过程不同于金属表面上的氢原子加成。

• Intermolecular dehydration: Ethanol → Diethyl ether

  质子化使一个乙醇分子的羟基成为更易离去的基团。另一个乙醇分子的氧取代水，随后去质子化生成乙醚；更强的脱水条件则有利于生成乙烯。

• Hydrolysis: Bromoethane → Ethanol

  氢氧根进攻与溴相连的饱和碳，同时 C-Br 键断裂。该伯底物的 SN2 路线以 OH 取代溴，并保留两个碳原子；水溶液条件较有利于这一取代分支，而非消去。

• Elimination: Bromoethane → Ethene

  碱移去与溴相邻的碳上的氢。溴离去时，C-H 键电子形成 C=C 的 π 键；该消去过程脱去 H 和 Br，而不改变两碳骨架。

• Cyanide substitution: Bromoethane → Propanenitrile

  氰根的碳端进攻溴乙烷的伯碳，溴离去。新形成的 C-C 键使氰根中的碳接到原碳链上，得到三碳腈，而不是乙腈。

• Ammonia substitution: Bromoethane → Ethylamine

  氨进攻与溴相连的碳，生成烷基铵中间体。另一分子氨移去质子，释放乙胺；若仍有卤代烷，产物还可进一步烷基化。

• Nitrile hydrolysis: Propanenitrile → Propanoic acid

  在酸促进下，水加成使腈先转化为酰胺，再经水解得到酸。腈基碳成为羧基碳，氮则以铵离子形式离开有机骨架。

• Nitrile reduction: Propanenitrile → Propylamine

  氢负离子加成还原碳氮三键；另行进行的水性后处理使含氮中间体质子化。腈基碳转化为 CH2NH2，保留扩展后的三碳骨架。

• Complete oxidation: Benzyl alcohol → Benzoic acid

  氧化先将苄位 CH2OH 转化为醛，再在碱性条件下转化为羧酸根。酸性后处理得到苯甲酸；芳环保留，侧链碳被进一步氧化。

• Carbonyl reduction: Benzaldehyde → Benzyl alcohol

  氢负离子进攻醛基碳，C=O 的 π 电子移向氧。醇盐质子化后得到苯甲醇；此过程不形成新的碳碳键，也不还原芳环。

• Aldehyde oxidation: Benzaldehyde → Benzoic acid

  水与醛可逆加成，形成可继续氧化的水合物。醛基碳成为羧基碳；酸性后处理使先形成的苯甲酸根转化为苯甲酸。

• Acyl chloride preparation: Benzoic acid → Benzoyl chloride

  与五氯化磷反应，以氯替代羧基中的 OH，保留酰基碳和芳环。新生成的酰氯更易发生亲核取代；其余原子进入 POCl3 和 HCl。

• Amide formation: Benzoyl chloride → Benzamide

  氨向酰基羰基加成，形成四面体中间体。羰基重新形成时排出氯离子，质子转移后生成苯甲酰胺；额外的氨捕获酸，形成氯化铵。

• Ester formation: Benzoyl chloride → Ethyl benzoate

  乙醇的氧进攻酰基羰基碳。氯离去和质子转移恢复 C=O 并生成酯；乙醇提供乙氧基，总反应同时生成 HCl。

• Amide formation: Acetyl chloride → Acetamide

  氨进攻羰基碳，四面体中间体消除时氯离去。去质子化生成乙酰胺，另一当量的氨中和酸，形成氯化铵。

• O acetylation: Salicylic acid → Aspirin

  水杨酸的酚氧从乙酸酐获得乙酰基。酰基取代形成酯，同时保留独立的羧基；质子转移生成伴生产物乙酸。

• N acetylation: Aniline → Acetanilide

  苯胺的氮进攻酸酐羰基，排出乙酸根来源的离去基团。质子转移形成乙酰苯胺和乙酸；产物中的氮与 C=O 相连，成为酰胺氮。

• Secondary alcohol oxidation: Cyclohexanol → Cyclohexanone

  氧化从 O-H 及羟基所连的碳上移去氢，形成 C=O。由于该碳原本连接另外两个碳，产物是酮，六元环保持不变。

• Ketone reduction: Cyclohexanone → Cyclohexanol

  氢负离子加成到平面羰基碳，π 电子移向氧。随后质子化生成环己醇，原有碳环保持完整。

• Amide hydrolysis: Acetamide → Ethanoic acid

  酸活化酰胺羰基，使水可加成。质子转移使含氮基团更易离去，随后 C-N 键断裂；酰基片段成为乙酸，氮最终成为铵离子。

• Catalytic oxidation: Methanol → Methanal

  从甲醇移去氢可形成羰基，同时保留其唯一的碳。在该催化氧化总反应中，氧接受被移去的氢，形成水。

• Carbonyl reduction: Methanal → Methanol

  氢负离子加成形成新的 C-H 键，并使 C=O 的 π 键转化为醇盐结构。随后质子化生成甲醇，不引入额外碳原子。

• Aldehyde oxidation: Methanal → Methanoic acid

  通过水合羰基的氧化，将醛转化为羧酸。碳原子数仍为一个，但还可能进一步氧化。

• Esterification: Methanol → Methyl acetate

  甲醇进攻被酸活化的羰基；经质子转移和脱水，形成乙酸甲酯。连接甲基的酯氧来自醇。

• Acid hydrolysis: Methyl acetate → Ethanoic acid

  水加成到质子化的酯羰基上。质子转移后，甲醇可在羰基重新形成时离去，同时生成酸和醇。

• Acid hydrolysis: Methyl acetate → Methanol

  水加成到质子化的酯羰基上。质子转移后，甲醇可在羰基重新形成时离去，同时生成酸和醇。

• Controlled oxidation: Butan-1-ol → Butanal

  氧化从 O-H 键及羟基所连的碳上移去氢，形成 C=O。及时分离生成的丁醛，可限制其进一步氧化。

• Carbonyl reduction: Butanal → Butan-1-ol

  氢负离子加成到醛基碳上，羰基氧成为醇盐。质子化后重新得到 1-丁醇。

• Aldehyde oxidation: Butanal → Butanoic acid

  水合的醛被氧化为羧基。原有的四个碳原子仍共同保留在丁酸中。

• Esterification: Butanoic acid → Ethyl butyrate

  乙醇氧与羧酸羰基碳成键，随后发生质子转移和脱水。产物由丁酰基片段与乙氧基连接而成。

• Acid hydrolysis: Ethyl butyrate → Butanoic acid

  水进攻与质子转移，使乙氧基片段以乙醇形式离去。另一部分重新形成羰基，生成丁酸。

• Acid hydrolysis: Ethyl butyrate → Ethanol

  水进攻与质子转移，使乙氧基片段以乙醇形式离去。另一部分重新形成羰基，生成丁酸。

• Esterification: Butan-1-ol → Butyl acetate

  醇氧进攻被活化的乙酸羰基。四碳链仍连接在氧上，二碳乙酰基片段提供羰基。

• Acid hydrolysis: Butyl acetate → Butan-1-ol

  水加成及质子转移后，水解断开酰基与氧的连接。原有丁基仍与氧相连，以 1-丁醇形式离去。

• Hydrobromination: Propene → 2-Bromopropane

  丙烯质子化时，生成仲碳正离子比生成伯碳正离子更有利。随后溴离子在中间的碳上形成 C-Br 键。

• Hydrolysis: 2-Bromopropane → Propan-2-ol

  以碳氧键替代碳溴键，生成 2-丙醇。中间碳仍为仲碳，因此后续氧化可生成丙酮。

• Esterification: Benzoic acid → Ethyl benzoate

  酸活化使乙醇可加成到苯甲酸上；经质子转移和脱水，形成苯甲酸乙酯。整个酰基取代过程中，芳环保持完整。

• Acid hydrolysis: Aspirin → Salicylic acid

  水进攻被酸活化的乙酰基羰基。酰基与氧的连接断裂并发生质子转移，恢复水杨酸的酚羟基；被移去的乙酰基形成乙酸。

• Alkaline hydrolysis and acidification: Methyl salicylate → Salicylic acid

  氢氧根加成到酯羰基，置换甲氧基片段，后者形成甲醇。在碱性条件下，水杨酸盐基团处于去质子化状态；随后酸化可恢复中性羧酸和酚羟基。