{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-03012762915d4ccdbd8b6fdfaf5ceb80","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"2f0b0594cb6a588a265c173f11e76185a50c8eb5da0a55a75d661ce92c1dcacf","doi":"10.1002/anie.201809929","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-0b2fc7615e7c93c8","route_slugs":["ord-03012762915d4ccdbd8b6fdfaf5ceb80-4355961f4127"],"reactant_slugs":["ord-compound-0c60f37e9afb6d8e49f9"],"product_slugs":["ord-compound-f3f356a16019db677b7c"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_689"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CC=CC1)N(CCCC)CCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25033-65-2"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[K].OC(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"865-47-4"}],"amount":{"moles":{"value":0.009,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.003,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C1C=CC=2C=CC=C(C3=CN=C(C=C3)C=4N=CC=CC4)C2N1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2098537-91-6"}],"amount":{"moles":{"value":0.007,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"In an argon filled glove box, a 5.0 mL wheaton microreactor was charged with [Ir(cod)(OMe)]2 (1.98 mg, 1.5 mol%), L1 ligand (2.1 mg, 3.5 mol%), B2pin2 (50.8 mg, 1.0 equiv.), KOtBu (1.0 mg, 4.5 mol%) and dry THF (1.0 mL). The reaction mixture was stirred for 2 minutes at room temperature. To this mixture, N,N-dibutylbenzamide (46.7 mg, 0.2 mmol) was added. The microreactor was capped with a teflon pressure cap and placed into pre-heated aluminum block at 80 oC. The reaction mixture was stirred for 12 h. After completion (judged by GC/MS), THF was removed under reduced pressure and chromatographic separation with silica gel (15% ethylacetate in hexane) gave the meta-borylated product 4e (49.6 mg, 69%) as oil."},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CC=C(C1)B2OC(C)(C)C(O2)(C)C)N(CCCC)CCCC"},{"type":"CAS_NUMBER","value":"2248763-83-7"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":69}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz, CDCl3): δ 7.82-7.78 (m, 2H), 7.44 (td, J= 7.6 Hz, J = 1.6 Hz, 1H), 7.40-7.36 (m, 1H), 3.49-3.45 (m, 2H), 3.17-3.14 (m, 2H), 1.65-1.62 (m, 2H), 1.52-1.47 (m, 2H), 1.42-1.39 (m, 2H), 1.34 (s, 12H), 1.14-1.12 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H), 0.78 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 171.5, 136.7, 135.2, 132.5, 129.2, 127.7, 83.9, 48.8, 44.5, 30.8, 29.7, 24.8, 20.3, 19.7, 13.9, 13.6.; 11B NMR (128 MHz, CDCl3): δ 30.1"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 360.2749","data":{"found":{"float_value":360.2749,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201809929"}}},"entities":[{"slug":"ord-compound-0c60f37e9afb6d8e49f9","name":"C15H23NO · ORD RYGJQVQEGCQNHM-UHFFFAOYSA-N","smiles":"CCCCN(CCCC)C(=O)c1ccccc1","inchi":"InChI=1S/C15H23NO/c1-3-5-12-16(13-6-4-2)15(17)14-10-8-7-9-11-14/h7-11H,3-6,12-13H2,1-2H3","formula":"C15H23NO"},{"slug":"ord-compound-f3f356a16019db677b7c","name":"C21H34BNO3 · ORD ZFPYVEOWHUBIFH-UHFFFAOYSA-N","smiles":"CCCCN(CCCC)C(=O)c1cccc(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C21H34BNO3/c1-7-9-14-23(15-10-8-2)19(24)17-12-11-13-18(16-17)22-25-20(3,4)21(5,6)26-22/h11-13,16H,7-10,14-15H2,1-6H3","formula":"C21H34BNO3"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-0b2fc7615e7c93c8","title":"Literature experiment — 10.1002/anie.201809929","source_type":"paper","doi":"10.1002/anie.201809929","url":"https://doi.org/10.1002/anie.201809929","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}