{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-05be27b392b147bd8a072d6a6d75c559","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"be11fc695ce92c34ff98a446b97461dea22159f32637b6f66ac830741db8fd70","doi":"10.1002/anie.201104544","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-1d9db24d746d4eac","route_slugs":["ord-05be27b392b147bd8a072d6a6d75c559-c837153662a2"],"reactant_slugs":["ord-compound-f59e049b76f83d54bc67"],"product_slugs":["ord-compound-7ceab2dd8ef2aaaeacc4"],"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_1285"},{"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=C(OC)C1C=2C=CC=C3C=CC=CC32"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1360606-92-3"}],"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":"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_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":0.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"Following the general procedure, column chromatography (EtOAc/nhexane 1:3) afforded 9g (125 mg, 69 %) as a light yellow viscous oil."},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=C(OC)C1C=2C(=CC=C3C=CC=CC32)B4OC(C)(C)C(O4)(C)C"},{"type":"CAS_NUMBER","value":"1360607-03-9"}],"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":"1 H NMR (500 MHz, CDCl3): δ = 8.35 (dd, 1H, J = 4.5, 1.0 Hz), 7.92 (d, 1H, J = 8.5 Hz), 7.89 (d, 1H, J = 8.5 Hz), 7.88 (d, 1H, J = 7.0 Hz), 7.49 (t, 1H, J = 8.0 Hz), 7.42 (d, 1H, J = 8.0 Hz), 7.38-7.34 (m, 2H), 7.28 (d, 1H, J =6.5 Hz), 3.69 (s, 3H), 1.15 (s, 12H); 13C NMR (125 MHz, CDCl3): δ = 154.8, 150.4, 143.1, 140.6, 134.8, 131.7, 130.5, 127.9, 127.2, 126.3, 125.7, 122.8, 117.2, 83.2, 55.5, 24.6 (C-B not observed); 11B NMR (160 MHz, CDCl3): δ = 30.4 ppm;"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 361.1854","data":{"found":{"float_value":361.1854,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201104544"}}},"entities":[{"slug":"ord-compound-f59e049b76f83d54bc67","name":"C16H13NO · ORD VTMISZOFKPHDIB-UHFFFAOYSA-N","smiles":"COc1cccnc1-c1cccc2ccccc12","inchi":"InChI=1S/C16H13NO/c1-18-15-10-5-11-17-16(15)14-9-4-7-12-6-2-3-8-13(12)14/h2-11H,1H3","formula":"C16H13NO"},{"slug":"ord-compound-7ceab2dd8ef2aaaeacc4","name":"C22H24BNO3 · ORD OMEIICZUICOOQK-UHFFFAOYSA-N","smiles":"COc1cccnc1-c1c(B2OC(C)(C)C(C)(C)O2)ccc2ccccc12","inchi":"InChI=1S/C22H24BNO3/c1-21(2)22(3,4)27-23(26-21)17-13-12-15-9-6-7-10-16(15)19(17)20-18(25-5)11-8-14-24-20/h6-14H,1-5H3","formula":"C22H24BNO3"}],"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"]}