{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-8a61495c860141f1a8046698b9543528","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"7d757185b338144e4c2294373ca7aa925f08f3e00576d1336185a0101f3a4dbf","doi":"10.1002/anie.201809929","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-0b2fc7615e7c93c8","route_slugs":["ord-8a61495c860141f1a8046698b9543528-77f23fdcdf57","ord-8a61495c860141f1a8046698b9543528-162e004bca35"],"reactant_slugs":["benzamide"],"product_slugs":["ord-compound-1aaca91716b9617e92b5","ord-compound-781399375d12bd4b6555"],"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_683"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(N)C=1C=CC=CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"55-21-0"}],"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":"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"}]},"reagent_2":{"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"}]},"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, benzamide (24.2 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. After 12 h, (judged by GC/MS), we found that the conversion was 23% and meta/para ratio was 1/1.5."},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(N)C1=CC=C(C=C1)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"179117-44-3"}],"measurements":[{"analysis_key":"product_1_MS","type":"YIELD","percentage":{"value":14}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(N)C=1C=CC=C(C1)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"188665-74-9"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":9}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_MS":{"type":"MS","details":"MS"},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1002/anie.201809929"}}},"entities":[{"slug":"benzamide","name":"Benzamide","smiles":"C1=CC=C(C=C1)C(=O)N","inchi":"InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)","formula":"C7H7NO"},{"slug":"ord-compound-1aaca91716b9617e92b5","name":"C13H18BNO3 · ORD NWEMAGLLVQDEKL-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccc(C(N)=O)cc2)OC1(C)C","inchi":"InChI=1S/C13H18BNO3/c1-12(2)13(3,4)18-14(17-12)10-7-5-9(6-8-10)11(15)16/h5-8H,1-4H3,(H2,15,16)","formula":"C13H18BNO3"},{"slug":"ord-compound-781399375d12bd4b6555","name":"C13H18BNO3 · ORD BPKIPHYWHVOWMS-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cccc(C(N)=O)c2)OC1(C)C","inchi":"InChI=1S/C13H18BNO3/c1-12(2)13(3,4)18-14(17-12)10-7-5-6-9(8-10)11(15)16/h5-8H,1-4H3,(H2,15,16)","formula":"C13H18BNO3"}],"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"]}