A Versatile Rhodium(I) Catalyst System for the Addition of Heteroarenes to both Alkenes and Alkynes by a C[BOND]H Bond Activation

Authors

  • Jaeyune Ryu,

    1. Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305–701 (Korea)
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  • Dr. Seung Hwan Cho,

    Corresponding author
    1. Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305–701 (Korea)
    • Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305–701 (Korea)
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  • Prof. Dr. Sukbok Chang

    Corresponding author
    1. Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305–701 (Korea)
    • Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305–701 (Korea)
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  • This research was supported by the Korea Research Foundation Grant (KRF-2008-C00024), MIRC (NRF-2011–0001322), a T. J. Park Postdoctoral Fellowship (S.H.C.), and a Global Ph.D. Fellowship (NRF-2011-0008452, J.R.).

Abstract

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Rhod to Addition: A highly efficient and convenient rhodium catalyst system was developed for the title transformation. A base co-catalyst was found to facilitate the key arene C[BOND]H bond-activation step and substrate scope was very broad, including both electron-deficient pyridine N-oxides, and electron-rich azoles. The catalytic system was effective for the hydroheteroarylation of both alkenes and alkynes and gave excellent regio- and stereoselectivity.

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