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Copper-Catalyzed Three-Component Borylstannylation of Alkynes

Authors

  • Yuki Takemoto,

    1. Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • Prof. Dr. Hiroto Yoshida,

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
    • Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • Prof. Dr. Ken Takaki

    1. Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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Abstract

Regio- and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three-component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic-borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of (Z)-tamoxifen with anti-breast cancer activity.

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