{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-039696dd0ae74ba58dd823308df27790","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"f396621f3b985c6804f5c7c579b3b2cf0a860fbfc3f815d748784851c1442cd9","doi":"10.1021/ja907700e","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-2c50030cbbcb7096","route_slugs":["ord-039696dd0ae74ba58dd823308df27790-7e91857be5cb","ord-039696dd0ae74ba58dd823308df27790-00d11b72f36a"],"reactant_slugs":["ord-compound-1ebe7b79c34da11da5be","ord-compound-a0b7b5b2ba43327b0cb6"],"product_slugs":["ord-compound-fd638e634c78253cd4a6"],"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":"875"}],"inputs":{"CCN(CC)C(=O)Oc1ccccc1/C=C/c2ccccc2":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1ccccc1/C=C/c2ccccc2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.184,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.0368,"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"}]}},"conditions":{"temperature":{"setpoint":{"value":150,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":10,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"C(=C\\c1ccccc1c2ccccc2)/c3ccccc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":93}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ja907700e"}}},"entities":[{"slug":"ord-compound-1ebe7b79c34da11da5be","name":"C19H21NO2 · ORD SACUBPAPXZNVAP-CCEZHUSRSA-N","smiles":"CCN(CC)C(=O)Oc1ccccc1/C=C/c1ccccc1","inchi":"InChI=1S/C19H21NO2/c1-3-20(4-2)19(21)22-18-13-9-8-12-17(18)15-14-16-10-6-5-7-11-16/h5-15H,3-4H2,1-2H3/b15-14+","formula":"C19H21NO2"},{"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-fd638e634c78253cd4a6","name":"C20H16 · ORD CBJPRTGKMYOVJO-FOCLMDBBSA-N","smiles":"C(=C\\c1ccccc1-c1ccccc1)/c1ccccc1","inchi":"InChI=1S/C20H16/c1-3-9-17(10-4-1)15-16-19-13-7-8-14-20(19)18-11-5-2-6-12-18/h1-16H/b16-15+","formula":"C20H16"}],"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-2c50030cbbcb7096","title":"Literature experiment — 10.1021/ja907700e","source_type":"paper","doi":"10.1021/ja907700e","url":"https://doi.org/10.1021/ja907700e","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"]}