Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety

Authors

  • Dr. Hikaru Yanai,

    Corresponding author
    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
    • School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Tasuku Yoshino,

    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Masaya Fujita,

    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Haruhiko Fukaya,

    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Dr. Akira Kotani,

    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Prof. Dr. Fumiyo Kusu,

    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Prof. Dr. Takeo Taguchi

    Corresponding author
    1. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
    • School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392 (Japan)
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  • Tf2CH2 was kindly provided by the Central Glass Co., Ltd. This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts” from the MEXT. We also thank the Asahi Glass Foundation.

Abstract

original image

A trifle of triflyl: N-substituted anilines react with 1,1,3,3-tetrakis(triflyl)propane to give a 2,2-bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).

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