{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-12ec8b3ea5864f8da66ba4813f640c50","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"c93a2110c5ba73900e1faac6cae3d55963918053d3cf96ac7e8c5c27bf7debf5","doi":"10.1002/anie.201610041","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-6b3986f4366fa19b","route_slugs":["ord-12ec8b3ea5864f8da66ba4813f640c50-0c4e660f8f7f"],"reactant_slugs":["ord-compound-d41d9a11780ecf6e8e43"],"product_slugs":["ord-compound-6255a151be739aef5cf4"],"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_902"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"S(C1=CC=CC(=C1)C(C)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1314900-80-5"}],"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":0.015,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"FC(F)(F)C1OB(OC1)C=2C=CC=CC2C=3C=NC(=CC3)C4=NC=CC=C4"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2060540-91-0"}],"amount":{"moles":{"value":0.03,"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":0.25,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=C(C=CC1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"106-42-3"}],"amount":{"volume":{"value":1.5000015,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":55,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"Ligand 3f: A mixture of ortho- and meta-borylated products (91 mg, 62% yield, ortho/meta + para = >30); ortho-borylated product 4l was obtained by further purification by GPC (80 mg, 54% yield), colorless oil;"},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC=C(C=C2SC)C(C)C"},{"type":"CAS_NUMBER","value":"2060541-15-1"}],"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":62}}],"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) 1.23 (d, J = 7.3 Hz, 6 H), 1 .36 (s, 12H), 2.46 (s, 3H), 2.89 (sep, J = 7.3Hz, 1H), 6.96 (d, J = 7.8 Hz, 1H), 7.02 (s, 1H), 7.64 (d, J = 7.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) 15.9, 24.0, 25.1, 34.7, 84.0, 112.1, 122.6, 136.6, 145.3, 152.6; meta-isomer: 1H NMR (400 MHz, CDCl3) 1.24 (d, J = 6.9 Hz, 6H), 1.34 (s, 12H), 2.49 (s, 3H), 2.89 (sep, J = 6.9 Hz, 1H), 7.23-7.24 (s, 1H), 7.43 (s, 1H), 7.52 (s, 1H); 13C NMR (100 MHz, CDCl3) 16.2, 24.2, 25.1, 34.4, 84.1, 128.2, 130.1, 130.5, 137.9, 149.0"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 315.1568","data":{"found":{"float_value":315.1568,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201610041"}}},"entities":[{"slug":"ord-compound-d41d9a11780ecf6e8e43","name":"C10H14S · ORD JXOLTWIALSFLTO-UHFFFAOYSA-N","smiles":"CSc1cccc(C(C)C)c1","inchi":"InChI=1S/C10H14S/c1-8(2)9-5-4-6-10(7-9)11-3/h4-8H,1-3H3","formula":"C10H14S"},{"slug":"ord-compound-6255a151be739aef5cf4","name":"C16H25BO2S · ORD BGYQKSOBPYKRRK-UHFFFAOYSA-N","smiles":"CSc1cc(C(C)C)ccc1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C16H25BO2S/c1-11(2)12-8-9-13(14(10-12)20-7)17-18-15(3,4)16(5,6)19-17/h8-11H,1-7H3","formula":"C16H25BO2S"}],"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-6b3986f4366fa19b","title":"Literature experiment — 10.1002/anie.201610041","source_type":"paper","doi":"10.1002/anie.201610041","url":"https://doi.org/10.1002/anie.201610041","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"]}