Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins

Authors

  • Dr. Bill Morandi,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • Zachary K. Wickens,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • Prof. Dr. Robert H. Grubbs

    Corresponding author
    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
    • Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA)
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  • We thank Scott Virgil and the Caltech Center for Catalysis for technical assistance. We gratefully acknowledge financial support from King Abdullah University of Science and Technology Center in Development, King Fahd University of Petroleum and Minerals, the NSF, and the Swiss National Science Foundation for a fellowship to B.M.

Abstract

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Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.

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