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Aryl[2-(hydroxypro-2-yl)cyclohyxyl]dimethylsilane: A Robust Aryl(trialkyl)silane Reagent for Nickel-catalyzed Cross-coupling Reactions with Aryl Tosylates

Authors

  • Dr. Shi Tang,

    1. College of Chemistry and Chemical Engineering, Jishou University, Renmin Road 120, Jishou 416000 (China), Fax: (+86) 0-743-856-3911
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  • Shu-Hua Li,

    1. College of Chemistry and Chemical Engineering, Jishou University, Renmin Road 120, Jishou 416000 (China), Fax: (+86) 0-743-856-3911
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  • Prof. Dr. Yoshiaki Nakao,

    Corresponding author
    1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)
    • Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)
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  • Prof. Dr. Tamejiro Hiyama

    Corresponding author
    1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)
    2. Current address: Research & Development Initiative, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan)
    • Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 (Japan)
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Abstract

A general route for the synthesis of an aryl(trialkyl)silane reagent, aryl[2-(hydroxypro-2-yl)cyclohexyl]dimethylsilane, is demonstrated. By using a carbonate salt as an activator, the robust aryl(trialkyl)silane promotes nickel-catalyzed aryl–aryl cross-coupling reactions with aryl tosylates in a fluoride-free and highly chemoselective manner. A reusable cyclic silyl ether was also quantitatively recovered.

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