Efficient Formation of Benzylic Quaternary Centers via Palladium Catalysis

Authors

  • Dr. Aditya L. Gottumukkala,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)
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  • Jasmin Suljagic,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)
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  • Dr. Kiran Matcha,

    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)
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  • Prof. Dr. Johannes G. de Vries,

    Corresponding author
    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)
    2. DSM Innovative Synthesis BV, P.O. Box 18, 6160 MD, Geleen (The Netherlands)
    • Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)

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  • Prof. Dr. Adriaan J. Minnaard

    Corresponding author
    1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)
    • Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands)

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Abstract

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Four′s a crowd: An efficient protocol for the formation of benzylic quaternary centers via arylation of enones using a catalyst made from Pd(O2CCF3)2 and 2,2′-bipyridine is developed. For cyclic substrates, catalyst loadings as low as 1 mol % Pd are enough to afford excellent yields (>90 %) using a variety of arylboronic acids. In case of acyclic substrates, the addition of KSbF6 was found to improve conversions and yields.

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