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

    Research output: Contribution to journalArticle

    8 Citations (Scopus)

    Abstract

    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
    Volume82
    Issue number9
    DOIs
    Publication statusPublished - 2017 May 5

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    Enantioselectivity
    Catalysts
    Stereoselectivity
    Ligands
    Acids

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction. / Nishimoto, Yoshio; Kondo, Hiroki; Yamaguchi, Kazuya; Yokogawa, Daisuke; Yamaguchi, Junichiro; Itami, Kenichiro; Irle, Stephan.

    In: Journal of Organic Chemistry, Vol. 82, No. 9, 05.05.2017, p. 4900-4906.

    Research output: Contribution to journalArticle

    Nishimoto, Yoshio ; Kondo, Hiroki ; Yamaguchi, Kazuya ; Yokogawa, Daisuke ; Yamaguchi, Junichiro ; Itami, Kenichiro ; Irle, Stephan. / Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 9. pp. 4900-4906.
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    AU - Yokogawa, Daisuke

    AU - Yamaguchi, Junichiro

    AU - Itami, Kenichiro

    AU - Irle, Stephan

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