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    Remote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C–C Bond Cleavage

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    Type
    Article
    Authors
    Huang, Long cc
    Ji, Tengfei
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2020-02-04
    Online Publication Date
    2020-02-04
    Print Publication Date
    2020-02-19
    Embargo End Date
    2021-02-04
    Submitted Date
    2019-11-20
    Permanent link to this record
    http://hdl.handle.net/10754/661459
    
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    Abstract
    Cross-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.
    Citation
    Huang, 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
    Sponsors
    The 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).
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/jacs.9b12490
    Additional Links
    https://pubs.acs.org/doi/10.1021/jacs.9b12490
    ae974a485f413a2113503eed53cd6c53
    10.1021/jacs.9b12490
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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