{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-06024163c8884fb49ab27a1eee76a484","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"f3beed4301a78779194f2beb6218535fe301b81092851155873278b5e20682f7","doi":"10.1002/chem.201103784","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-7ede0b389b2328fc","route_slugs":["ord-06024163c8884fb49ab27a1eee76a484-a970fdabd5d9","ord-06024163c8884fb49ab27a1eee76a484-a947e8477b25"],"reactant_slugs":["ord-compound-fc88b5e678a48b24f8a1","ord-compound-acaf2ca60cd6901ee4ae"],"product_slugs":["ord-compound-7566804a38d474eeb63e"],"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":"1193"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.04,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"COc2ccc1cc(CCO[Si](C)(C)C(C)(C)C)ccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"COc2ccc1cc(CCO[Si](C)(C)C(C)(C)C)ccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"C[Zn](C)(C)([Li])([Li])c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[Zn](C)(C)([Li])([Li])c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":9,"precision":3,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)[Si](C)(C)OCCc3ccc2cc(c1ccccc1)ccc2c3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":67}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/chem.201103784"}}},"entities":[{"slug":"ord-compound-fc88b5e678a48b24f8a1","name":"C19H28O2Si · ORD RMHPAOHIVIOGON-UHFFFAOYSA-N","smiles":"COc1ccc2cc(CCO[Si](C)(C)C(C)(C)C)ccc2c1","inchi":"InChI=1S/C19H28O2Si/c1-19(2,3)22(5,6)21-12-11-15-7-8-17-14-18(20-4)10-9-16(17)13-15/h7-10,13-14H,11-12H2,1-6H3","formula":"C19H28O2Si"},{"slug":"ord-compound-acaf2ca60cd6901ee4ae","name":"C9H14Li2Zn · ORD UEBHSGDLLXKCML-UHFFFAOYSA-N","smiles":"[Li][Zn]([Li])([CH3])([CH3])([CH3])[c]1ccccc1","inchi":"InChI=1S/C6H5.3CH3.2Li.Zn/c1-2-4-6-5-3-1;;;;;;/h1-5H;3*1H3;;;","formula":"C9H14Li2Zn"},{"slug":"ord-compound-7566804a38d474eeb63e","name":"C24H30OSi · ORD MMBHGMSMFHDRBB-UHFFFAOYSA-N","smiles":"CC(C)(C)[Si](C)(C)OCCc1ccc2cc(-c3ccccc3)ccc2c1","inchi":"InChI=1S/C24H30OSi/c1-24(2,3)26(4,5)25-16-15-19-11-12-23-18-22(14-13-21(23)17-19)20-9-7-6-8-10-20/h6-14,17-18H,15-16H2,1-5H3","formula":"C24H30OSi"}],"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-7ede0b389b2328fc","title":"Literature experiment — 10.1002/chem.201103784","source_type":"paper","doi":"10.1002/chem.201103784","url":"https://doi.org/10.1002/chem.201103784","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"]}