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Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors

Authors

  • Jeffrey C. Holder,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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    • These authors have contributed equally.

  • Dr. Alexander N. Marziale,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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    • These authors have contributed equally.

  • Dr. Michele Gatti,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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  • Bin Mao,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
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  • Prof. Brian M. Stoltz

    Corresponding author
    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
    • Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd, MC 101-20, Pasadena, CA 91125 (USA)
    Search for more papers by this author

Abstract

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Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

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