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Borylcyanocuprate in a One-Pot Carboboration by a Sequential Reaction with an Electron-Deficient Alkyne and an Organic Carbon Electrophile

Authors

  • Yuri Okuno,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656 Tokyo (Japan), Fax: (+81) 3-5841-7263
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  • Dr. Makoto Yamashita,

    Corresponding author
    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656 Tokyo (Japan), Fax: (+81) 3-5841-7263
    • Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656 Tokyo (Japan), Fax: (+81) 3-5841-7263
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  • Prof. Dr. Kyoko Nozaki

    Corresponding author
    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656 Tokyo (Japan), Fax: (+81) 3-5841-7263
    • Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656 Tokyo (Japan), Fax: (+81) 3-5841-7263
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  • This work was supported by Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering) and by KAKENHI (21245023 and 21685006) from MEXT (Japan).

Abstract

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A key reactive species, lithium borylcyanocuprate, was isolated and fully characterized in a one-pot carboboration of alkynes. The carboboration involves a boryllithium, CuCN⋅2 LiCl, an ester-substituted alkyne, and an organic electrophile (see scheme). By changing the reaction temperature, the syn/anti ratio of the carboborated products can also be changed.

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