{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-03493c8fbc6d4f73b834a599f010615a","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"eedc9c6b57cacd5dfbf0deffd9977754e54423acca483a6552fb5a4c2cbad81a","doi":"10.1002/anie.201708967","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-c772e94b40b29614","route_slugs":["ord-03493c8fbc6d4f73b834a599f010615a-4d47cf859b98","ord-03493c8fbc6d4f73b834a599f010615a-1fa087537b88"],"reactant_slugs":["ord-compound-82f2baf180b88c9843a8"],"product_slugs":["ord-compound-3cc5a6c24d1f2085485f","ord-compound-0fcbb012213cc00feb5e"],"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_463"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC=1C=CC=CC1C(F)(F)F)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"304664-21-9"}],"amount":{"moles":{"value":0.25,"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":0.00375,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"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":0.375,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)([O-])CC=1C=NC(=CC1)C2=NC=C(C=C2)C.CCCC[N+](CCCC)(CCCC)CCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2007932-96-7"}],"amount":{"moles":{"value":0.0075,"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":1.25,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"Following general procedure F using N‐(2‐(trifluoromethyl)benzyl)pivalamide (64.8 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1A (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction wasstirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 3.8:1 meta:para borylation in 91% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐ 60):EtOAc (19:1‐6:4) to give the title compound (as a 3.0:1 mixture of meta:para ratio as determined by 1 H NMR) as a white solid (69.1 mg, 0.18 mmol, 72%). Using a combination of 2D NMR analysis the meta and para isomers are described:"},"outcomes":[{"reaction_time":{"value":20,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC1=CC(=CC=C1C(F)(F)F)B2OC(C)(C)C(O2)(C)C)C(C)(C)C"},{"type":"CAS_NUMBER","value":"2135636-82-5"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":72}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(NCC1=CC=C(C=C1C(F)(F)F)B2OC(C)(C)C(O2)(C)C)C(C)(C)C"},{"type":"CAS_NUMBER","value":"2135636-83-6"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":19}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"Meta 1 H NMR (600 MHz, CDCl3) δ 7.87 (s, 1H), 7.79 (d, J = 7.6 Hz, 1H), 7.63 (d, J = 7.6 Hz, 1H), 6.00 (br s, 1H), 4.60 (d, J = 5.8 Hz, 2H), 1.33 (s, 12H), 1.21 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 178.1, 136.5, 135.6, 133.8, 130. (q, 2 JC‐F = 30 Hz), 125.3 (q, 2 JC‐F = 5 Hz), 124.4 (q, 1 JC‐F = 274 Hz), 84.3, 40.5 (q, 3 JC‐F = 2 Hz), 38.7, 27.4, 24.8; Para 1 H NMR (600 MHz, CDCl3) δ 8.06 (s, 1H), 7.92 (d, J = 7.7 Hz, 1H), 7.50 (d, J = 7.7 Hz, 1H), 6.07 (br t, J = 5.3 Hz, 1H), 4.60 (d, J = 5.8 Hz, 2H), 1.34 (s, 12H), 1.18 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 178.2, 139.8, 138.6, 132.1 (q, 3 JC‐F = 5 Hz), 129.8, 127.5 (q, 2 JC‐F = 31 Hz), 124.5 (q, 1 JC‐F = 275 Hz), 84.2, 40.3 (q, 3 JC‐F = 2 Hz), 38.7, 27.4, 24.8."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Expected: 386.2109 Found: 386.2091","data":{"expected":{"float_value":386.2109,"description":"Expected m/z"},"found":{"float_value":386.2091,"description":"Observed m/z"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1002/anie.201708967"}}},"entities":[{"slug":"ord-compound-82f2baf180b88c9843a8","name":"C13H16F3NO · ORD MJALYHCWBYHLDF-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)NCc1ccccc1C(F)(F)F","inchi":"InChI=1S/C13H16F3NO/c1-12(2,3)11(18)17-8-9-6-4-5-7-10(9)13(14,15)16/h4-7H,8H2,1-3H3,(H,17,18)","formula":"C13H16F3NO"},{"slug":"ord-compound-3cc5a6c24d1f2085485f","name":"C19H27BF3NO3 · ORD RRECHEYWZXAEHZ-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)NCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(F)(F)F","inchi":"InChI=1S/C19H27BF3NO3/c1-16(2,3)15(25)24-11-12-10-13(8-9-14(12)19(21,22)23)20-26-17(4,5)18(6,7)27-20/h8-10H,11H2,1-7H3,(H,24,25)","formula":"C19H27BF3NO3"},{"slug":"ord-compound-0fcbb012213cc00feb5e","name":"C19H27BF3NO3 · ORD FMFJQILJSXJJER-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)NCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(F)(F)F","inchi":"InChI=1S/C19H27BF3NO3/c1-16(2,3)15(25)24-11-12-8-9-13(10-14(12)19(21,22)23)20-26-17(4,5)18(6,7)27-20/h8-10H,11H2,1-7H3,(H,24,25)","formula":"C19H27BF3NO3"}],"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-c772e94b40b29614","title":"Literature experiment — 10.1002/anie.201708967","source_type":"paper","doi":"10.1002/anie.201708967","url":"https://doi.org/10.1002/anie.201708967","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"]}