{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0258ea754df147698be2b7409a47f743","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"df956355c14bbfce7b1ba5ea55754bc1070b19e980caf21f13b5a8ed8b18249a","doi":"10.1021/ja200398c","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-eb9e45f2bd5aabe4","route_slugs":["ord-0258ea754df147698be2b7409a47f743-ccebfe4f1ac4","ord-0258ea754df147698be2b7409a47f743-7fe4cd5473bf"],"reactant_slugs":["ord-compound-484401d33ecfce399352","ord-compound-a0b7b5b2ba43327b0cb6"],"product_slugs":["ord-compound-36deee734b7cffe424eb"],"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.","Some source yields use float_value rather than a typed percentage; the original value is retained without asserting units.","At least one source reactant quantity is zero; no stoichiometric amount is inferred from this placeholder."],"raw":{"identifiers":[{"type":"REACTION_TYPE","value":"925"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.0878,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"OB(O)c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"OB(O)c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CCN(CC)C(=O)Oc1cccc2ccccc12":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1cccc2ccccc12"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.439,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":150,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12.5,"precision":7.5,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc(c1cccc2ccccc12)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":82}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ja200398c"}}},"entities":[{"slug":"ord-compound-484401d33ecfce399352","name":"C15H17NO2 · ORD PCEIRTKGPDXWOT-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1cccc2ccccc12","inchi":"InChI=1S/C15H17NO2/c1-3-16(4-2)15(17)18-14-11-7-9-12-8-5-6-10-13(12)14/h5-11H,3-4H2,1-2H3","formula":"C15H17NO2"},{"slug":"ord-compound-a0b7b5b2ba43327b0cb6","name":"C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N","smiles":"OB(O)c1ccccc1","inchi":"InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H","formula":"C6H7BO2"},{"slug":"ord-compound-36deee734b7cffe424eb","name":"C16H12 · ORD IYDMICQAKLQHLA-UHFFFAOYSA-N","smiles":"c1ccc(-c2cccc3ccccc23)cc1","inchi":"InChI=1S/C16H12/c1-2-7-13(8-3-1)16-12-6-10-14-9-4-5-11-15(14)16/h1-12H","formula":"C16H12"}],"dataset":{"dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","name":"NiCOlit","description":"Nickel-catalyzed cross-couplings extracted from organic reaction publications","records_in_source":1762,"path":"data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","sha256":"195765643b4aaad79d9ed82de6737a4855b9f2716e0bc0aa10cff950b7604d39","bytes":126909,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet"},"publication":{"slug":"ord-publication-eb9e45f2bd5aabe4","title":"Literature experiment — 10.1021/ja200398c","source_type":"paper","doi":"10.1021/ja200398c","url":"https://doi.org/10.1021/ja200398c","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"]}