Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction

Yoshio Nishimoto, Hiroki Kondo, Kazuya Yamaguchi, Daisuke Yokogawa, Junichiro Yamaguchi, Kenichiro Itami, Stephan Irle

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    The mechanism of an aromatic C-H coupling reaction between heteroarenes and arylboronic acids using a Pd catalyst was theoretically and experimentally investigated. We identified the C-B transmetalation as the rate-determining step. The (S)-catalyst-reactant complex was found to be stabilized by hyperconjugation between π-orbitals on the tolyl group and the S-O σ* antibonding orbital in the catalyst ligand. Our findings suggest routes for the design of new, improved Pd catalysts with higher stereoselectivity.

    Original languageEnglish
    Pages (from-to)4900-4906
    Number of pages7
    JournalJournal of Organic Chemistry
    Issue number9
    Publication statusPublished - 2017 May 5


    ASJC Scopus subject areas

    • Organic Chemistry

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