{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-004434c61c3445ce81796e8a4175144e","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"2a4fc734738dcaa676560ef9440d36cb3635dac9ee2e3e126d9a3341fe5c47e2","doi":"10.1021/acscatal.7b01058","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-9a11d7e4fb836903","route_slugs":["ord-004434c61c3445ce81796e8a4175144e-03104b52001c","ord-004434c61c3445ce81796e8a4175144e-7fa6960f66df"],"reactant_slugs":["ord-compound-c4224958bee37ded911e","ord-compound-80357aa67de73bc4db54"],"product_slugs":["ord-compound-4f2243157c7472927cc1"],"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":"1733"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)C[Al](CC(C)C)c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)C[Al](CC(C)C)c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CC(C)(C)OC(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)OC(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc(c2ccc1ccccc1c2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":51}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acscatal.7b01058"}}},"entities":[{"slug":"ord-compound-c4224958bee37ded911e","name":"C15H16O3 · ORD CUFPXYFHDGLCPI-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Oc1ccc2ccccc2c1","inchi":"InChI=1S/C15H16O3/c1-15(2,3)18-14(16)17-13-9-8-11-6-4-5-7-12(11)10-13/h4-10H,1-3H3","formula":"C15H16O3"},{"slug":"ord-compound-80357aa67de73bc4db54","name":"C14H23Al · ORD MSZVPIUTCYUSLM-UHFFFAOYSA-N","smiles":"CC(C)[CH2][Al]([CH2]C(C)C)[c]1ccccc1","inchi":"InChI=1S/C6H5.2C4H9.Al/c1-2-4-6-5-3-1;2*1-4(2)3;/h1-5H;2*4H,1H2,2-3H3;","formula":"C14H23Al"},{"slug":"ord-compound-4f2243157c7472927cc1","name":"C16H12 · ORD TURIHPLQSRVWHU-UHFFFAOYSA-N","smiles":"c1ccc(-c2ccc3ccccc3c2)cc1","inchi":"InChI=1S/C16H12/c1-2-6-13(7-3-1)16-11-10-14-8-4-5-9-15(14)12-16/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-9a11d7e4fb836903","title":"Literature experiment — 10.1021/acscatal.7b01058","source_type":"paper","doi":"10.1021/acscatal.7b01058","url":"https://doi.org/10.1021/acscatal.7b01058","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"]}