{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-8c8d5cbe7313457197480b73e68c5e45","dataset_id":"ord_dataset-89b083710e2d441aa0040c361d63359f","reaction_class":"Decarboxylative sp3–sp2 cross-coupling","transformation_sha256":"4de256c3793fe5f9141044c741c6326e5cf0ba160d098b1dd3072dcedb282e85","doi":"10.1126/science.1255525","dataset_source_slug":"ord-dataset-89b083710e2d441aa0040c361d63359f","publication_source_slug":"ord-publication-434e04daf25acf3e","route_slugs":["ord-8c8d5cbe7313457197480b73e68c5e45-e64c8672bf61","ord-8c8d5cbe7313457197480b73e68c5e45-f45df44929bf"],"reactant_slugs":["ord-compound-8344946db561ec57b94d","ord-compound-107a56b73192e42c88c9"],"product_slugs":["ord-compound-2eb5af7dc0ca907d3f3e"],"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 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brine","input":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"NAME","value":"water"}]},{"identifiers":[{"type":"SMILES","value":"[Na+].[Cl-]"},{"type":"NAME","value":"NaCl"}]}]}},{"type":"DRY_WITH_MATERIAL","details":"dried over MgSO4"},{"type":"CONCENTRATION","details":"concentrated in vacuo"},{"type":"FLASH_CHROMATOGRAPHY","details":"Fluka, 230-400 mesh, solvent system: 12% ethyl acetate/hexane"}],"outcomes":[{"reaction_time":{"value":72,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(=O)C1=CC=C(C(Cc2cn(C(=O)OC(C)(C)C)c3ccccc23)NC(=O)OC(C)(C)C)C=C1"}],"is_desired_product":true,"measurements":[{"analysis_key":"1h nmr","type":"IDENTITY"},{"analysis_key":"13c 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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"]}