{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0837ae1efc6d4b7fb5b2a67ee40ac839","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"78c7bcd644ec59475a843c3218a1e1fbc3219df6cf422199e6240a45e61b47c8","doi":"10.1002/anie.201104544","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-1d9db24d746d4eac","route_slugs":["ord-0837ae1efc6d4b7fb5b2a67ee40ac839-8ed097063fa1"],"reactant_slugs":["ord-compound-405196c1d3be75cad24e"],"product_slugs":["ord-compound-8510dfa1a28f6d96a0bb"],"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_1281"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"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"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=2C=CC=CC2C1C=3C=CC4=C5C3C=CC=C5CC4"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1360606-90-1"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"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":0.0025,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":0.025,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=CC1C=NN(CC=2C=CC=CC2)CC=3C=CC=CC3"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"237402-29-8"}],"amount":{"moles":{"value":0.005,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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":0.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"Following the general procedure, column chromatography (EtOAc/nhexane 1:4) afforded 9c (160 mg, 79 %) as a yellow solid."},"outcomes":[{"reaction_time":{"value":7,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=2C=CC=CC2C1C=3C(=CC4=C5C3C=CC=C5CC4)B6OC(C)(C)C(O6)(C)C"},{"type":"CAS_NUMBER","value":"1360606-96-7"}],"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":79}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, CDCl3): δ = 8.66 (d, 1H, J = 6.0 Hz), 7.88 (d, 1H, J = 8.5 Hz), 7.78 (s, 1H), 7.71 (d, 1H, J = 6.0 Hz), 7.63 (t, 1H, J = 7.5 Hz), 7.52 (d, 1H, J = 8.5 Hz), 7.33 (d, 1H, J = 7.5 Hz), 7.32-7.27 (m, 2H), 7.06 (d, 1H, J = 7.0 Hz), 3.48 (s, 4H), 0.86 (s, 12H); 13C NMR (100 MHz, CDCl3): δ = 161.4, 145.8, 145.6, 141.4, 140.6, 136.2, 130.7, 129.8, 129.5, 128.0, 127.9, 126.7, 126.4, 123.8, 121.6, 120.3, 119.5, 83.2, 30.5, 30.2, 24.3 (C-B not observed); 11B NMR (160 MHz, CDCl3): δ = 30.3 ppm;"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 407.2055","data":{"found":{"float_value":407.2055,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201104544"}}},"entities":[{"slug":"ord-compound-405196c1d3be75cad24e","name":"C21H15N · ORD IYOWVDAWQANKHJ-UHFFFAOYSA-N","smiles":"c1ccc2c(-c3ccc4c5c(cccc35)CC4)nccc2c1","inchi":"InChI=1S/C21H15N/c1-2-6-17-14(4-1)12-13-22-21(17)19-11-10-16-9-8-15-5-3-7-18(19)20(15)16/h1-7,10-13H,8-9H2","formula":"C21H15N"},{"slug":"ord-compound-8510dfa1a28f6d96a0bb","name":"C27H26BNO2 · ORD DAFGOMSOCOTYCA-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc3c4c(cccc4c2-c2nccc4ccccc24)CC3)OC1(C)C","inchi":"InChI=1S/C27H26BNO2/c1-26(2)27(3,4)31-28(30-26)22-16-19-13-12-18-9-7-11-21(23(18)19)24(22)25-20-10-6-5-8-17(20)14-15-29-25/h5-11,14-16H,12-13H2,1-4H3","formula":"C27H26BNO2"}],"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-1d9db24d746d4eac","title":"Literature experiment — 10.1002/anie.201104544","source_type":"paper","doi":"10.1002/anie.201104544","url":"https://doi.org/10.1002/anie.201104544","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"]}