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Aerobic Oxidative Heck/Dehydrogenation Reactions of Cyclohexenones: Efficient Access to meta-Substituted Phenols

Authors

  • Yusuke Izawa,

    1. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
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    • These authors contributed equally to this work.

  • Dr. Changwu Zheng,

    1. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
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    • These authors contributed equally to this work.

  • Prof. Shannon S. Stahl

    Corresponding author
    1. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
    • Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)===

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  • We thank Dr. Doris Pun for assistance in product purification. Financial support was provided by the NIH (R01 GM100143), Mitsubishi Chemical Corporation, and the Shanghai Institute of Organic Chemistry (postdoctoral fellowship for C.W.Z.).

Abstract

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Jockeying for the (meta)position: A new dicationic palladium(II) catalyst, employing a 6,6′-dimethyl-2,2′-bipyridine ligand, promotes both the aerobic oxidative Heck coupling and dehydrogenation reactions of cyclohexenones. These reactions may be combined in a one-pot sequence to enable the straightforward synthesis of meta-substituted phenols (see scheme).

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