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Copper(I) Enolate Complexes in α-Arylation Reactions: Synthesis, Reactivity, and Mechanism

Authors

  • Dr. Zheng Huang,

    1. Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)
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  • Prof. Dr. John F. Hartwig

    Corresponding author
    1. Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)
    2. Current address: University of California, Department of Chemistry, 718 Latimer Hall, Berkeley, CA 94720 (USA)
    • Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, IL 61801 (USA)
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  • We thank the NIH (GM-58108) for support of this work.

Abstract

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Copper is all bound up: The copper-catalyzed α-arylation of carbonyl compounds occurs through oxidative addition of iodoarenes to the C-bound CuI enolate species 1 to form an aryl–CuIII intermediate (see scheme). Computational results provide insight into the origins of the relative reactivity of various CuI enolate complexes in the reactions with iodoarenes.

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