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dc.contributor.authorHuang, Long
dc.contributor.authorJi, Tengfei
dc.contributor.authorRueping, Magnus
dc.date.accessioned2020-02-11T06:07:16Z
dc.date.available2020-02-11T06:07:16Z
dc.date.issued2020-02-04
dc.date.submitted2019-11-20
dc.identifier.citationHuang, L., Ji, T., & Rueping, M. (2020). Remote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C–C Bond Cleavage. Journal of the American Chemical Society. doi:10.1021/jacs.9b12490
dc.identifier.doi10.1021/jacs.9b12490
dc.identifier.urihttp://hdl.handle.net/10754/661459
dc.description.abstractCross-coupling reactions for carbon–carbon and carbon–heteroatom bond formation are of great importance in modern chemical synthesis. In addition to classical cross-couplings involving preformed or preactivated coupling partners, more recently breakthroughs have been made in the selective, direct coupling of abundant aliphatic carbon–hydrogen bonds using hydrogen atom transfer reactions in which the bond-dissociation energy is the thermodynamic driving force. The more challenging carbon–carbon bond activation is still rather underdeveloped due to the bond inertness. Herein, we report a mild and general strategy for the activation of a diverse set of readily available cyclic alcohols for the remote and site-specific arylation of ketones via the combination of photoredox-mediated multisite concerted proton–electron transfer (MS-PCET) and nickel catalysis. The current cross-coupling proceeds with the generation of an alkoxy radical utilizing bond-dissociation free energy (BDFE) as the thermodynamic driving force. Subsequently, the resulting remote carbon-centered radicals formed by C–C cleavage merge with the nickel catalytic cycle to create the challenging C(sp3)–C(sp2) bonds.
dc.description.sponsorshipThe authors acknowledge King Abdullah University of Science and Technology (KAUST) for support. The research leading to these results has also received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement no. 617044 (SunCatChem).
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/jacs.9b12490
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/jacs.9b12490.
dc.titleRemote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C–C Bond Cleavage
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalJournal of the American Chemical Society
dc.rights.embargodate2021-02-04
dc.eprint.versionPost-print
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
kaust.personRueping, Magnus
dc.date.accepted2020-02-04
refterms.dateFOA2020-02-11T10:39:19Z
dc.date.published-online2020-02-04
dc.date.published-print2020-02-19


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