{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-50558bf0af724e9795914b366e8ae49b","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"e98b2d06d5d3d902e34976b097acee259e69efe13d538ac803b0c5ea2e05986d","doi":"10.1021/jacs.7b04279","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-a617035187d97090","route_slugs":["ord-50558bf0af724e9795914b366e8ae49b-7d274dd32b96","ord-50558bf0af724e9795914b366e8ae49b-285389c15d75"],"reactant_slugs":["ord-compound-cd300a3a60ea7b1be12f","ord-compound-562366bda5adaac8f422"],"product_slugs":["ord-compound-42ea23ffc848ca15f4a8"],"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":"1728"}],"inputs":{"CC2(C)COB(c1ccccc1)OC2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC2(C)COB(c1ccccc1)OC2"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"COc2ccc(c1ccccc1)cc2":{"components":[{"identifiers":[{"type":"SMILES","value":"COc2ccc(c1ccccc1)cc2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"ICy":{"components":[{"identifiers":[{"type":"NAME","value":"ICy"}],"amount":{"moles":{"value":0.060000002,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":120,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc(c2ccc(c1ccccc1)cc2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":71}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/jacs.7b04279"}}},"entities":[{"slug":"ord-compound-cd300a3a60ea7b1be12f","name":"C11H15BO2 · ORD FQMSNYZDFMWLGC-UHFFFAOYSA-N","smiles":"CC1(C)COB(c2ccccc2)OC1","inchi":"InChI=1S/C11H15BO2/c1-11(2)8-13-12(14-9-11)10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3","formula":"C11H15BO2"},{"slug":"ord-compound-562366bda5adaac8f422","name":"C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N","smiles":"COc1ccc(-c2ccccc2)cc1","inchi":"InChI=1S/C13H12O/c1-14-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3","formula":"C13H12O"},{"slug":"ord-compound-42ea23ffc848ca15f4a8","name":"C18H14 · ORD XJKSTNDFUHDPQJ-UHFFFAOYSA-N","smiles":"c1ccc(-c2ccc(-c3ccccc3)cc2)cc1","inchi":"InChI=1S/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H","formula":"C18H14"}],"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-a617035187d97090","title":"Literature experiment — 10.1021/jacs.7b04279","source_type":"paper","doi":"10.1021/jacs.7b04279","url":"https://doi.org/10.1021/jacs.7b04279","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"]}