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dc.contributor.authorOcchialini, Gino
dc.contributor.authorPalani, Vignesh
dc.contributor.authorWendlandt, Alison E
dc.date.accessioned2022-03-21T14:14:05Z
dc.date.available2022-03-21T14:14:05Z
dc.date.issued2022-01-12
dc.identifier.urihttps://hdl.handle.net/1721.1/141321
dc.description.abstractThe positional isomerization of C═C double bonds is a powerful strategy for the interconversion of alkene regioisomers. However, existing methods provide access to thermodynamically more stable isomers from less stable starting materials. Here, we report the discovery of a dual catalyst system that promotes contra-thermodynamic positional alkene isomerization under photochemical irradiation, providing access to terminal alkene isomers directly from conjugated, internal alkene starting materials. The utility of the method is demonstrated in the deconjugation of diverse electron-rich/electron-poor alkenes and through strategic application to natural product synthesis. Mechanistic studies are consistent with a regiospecific bimolecular homolytic substitution (SH2') mechanism proceeding through an allyl-cobaloxime intermediate.en_US
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionof10.1021/jacs.1c12043en_US
dc.rightsCreative Commons Attribution-Noncommercial-Share Alikeen_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/en_US
dc.sourcechemRxiven_US
dc.titleCatalytic, contra-Thermodynamic Positional Alkene Isomerizationen_US
dc.typeArticleen_US
dc.identifier.citationOcchialini, Gino, Palani, Vignesh and Wendlandt, Alison E. 2022. "Catalytic, contra-Thermodynamic Positional Alkene Isomerization." Journal of the American Chemical Society, 144 (1).
dc.relation.journalJournal of the American Chemical Societyen_US
dc.eprint.versionOriginal manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/NonPeerRevieweden_US
dc.date.updated2022-03-21T13:59:30Z
dspace.orderedauthorsOcchialini, G; Palani, V; Wendlandt, AEen_US
dspace.date.submission2022-03-21T13:59:31Z
mit.journal.volume144en_US
mit.journal.issue1en_US
mit.licenseOPEN_ACCESS_POLICY
mit.metadata.statusAuthority Work and Publication Information Neededen_US


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