{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-04f9b8bd7c1241548bf7d58f4d10942b","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"d966a533c4202d49a2ef9daf780461ca80d78969136e97bf29bb97fdbe7acd67","doi":"10.1021/ja412107b","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-d34e172d11635b5d","route_slugs":["ord-04f9b8bd7c1241548bf7d58f4d10942b-836bef379996","ord-04f9b8bd7c1241548bf7d58f4d10942b-04c5eebf6af5"],"reactant_slugs":["ord-compound-67d97c22440781269217","ord-compound-c1a2152c999c8c5edd35"],"product_slugs":["ord-compound-541295949f24edb9fd4a"],"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":"556"}],"inputs":{"CC[Si](CC)(CC)B1OC(C)(C)C(C)(C)O1":{"components":[{"identifiers":[{"type":"SMILES","value":"CC[Si](CC)(CC)B1OC(C)(C)C(C)(C)O1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CC(C)(C)C(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.25,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC[Si](CC)(CC)c2ccc1ccccc1c2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":1}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/ja412107b"}}},"entities":[{"slug":"ord-compound-67d97c22440781269217","name":"C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)Oc1ccc2ccccc2c1","inchi":"InChI=1S/C15H16O2/c1-15(2,3)14(16)17-13-9-8-11-6-4-5-7-12(11)10-13/h4-10H,1-3H3","formula":"C15H16O2"},{"slug":"ord-compound-c1a2152c999c8c5edd35","name":"C12H27BO2Si · ORD IUQZZPMFYLUYJJ-UHFFFAOYSA-N","smiles":"CC[Si](CC)(CC)B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C12H27BO2Si/c1-8-16(9-2,10-3)13-14-11(4,5)12(6,7)15-13/h8-10H2,1-7H3","formula":"C12H27BO2Si"},{"slug":"ord-compound-541295949f24edb9fd4a","name":"C16H22Si · ORD IFSRZMLTNKGPIF-UHFFFAOYSA-N","smiles":"CC[Si](CC)(CC)c1ccc2ccccc2c1","inchi":"InChI=1S/C16H22Si/c1-4-17(5-2,6-3)16-12-11-14-9-7-8-10-15(14)13-16/h7-13H,4-6H2,1-3H3","formula":"C16H22Si"}],"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-d34e172d11635b5d","title":"Literature experiment — 10.1021/ja412107b","source_type":"paper","doi":"10.1021/ja412107b","url":"https://doi.org/10.1021/ja412107b","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"]}