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Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes

Authors

  • Andreas K. Å. Persson,

    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden), Fax: (+46) 8-154-908
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  • Tuo Jiang,

    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden), Fax: (+46) 8-154-908
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  • Magnus T. Johnson,

    1. Department of Chemistry, Organic Chemistry, Lund University, P.O. Box 124, 22100 Lund (Sweden)
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  • Prof. Jan-E. Bäckvall

    Corresponding author
    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden), Fax: (+46) 8-154-908
    • Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden), Fax: (+46) 8-154-908
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  • Financial support from the European Research Council (ERC AdG 247014), the Swedish Research Council, the Berzelii Center EXSELENT, and the Knut and Alice Wallenberg Foundation is gratefully acknowledged.

Abstract

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An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron-transfer reagent, and 1,4-benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.

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