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Functional-Group-Tolerant Catalytic Migratory Oxidative Coupling of Nitrones

Authors

  • Shogo Hashizume,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-5206
    2. Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Kounosuke Oisaki,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-5206
    2. Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-5206

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  • Prof. Dr. Motomu Kanai

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-5206
    2. Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-5206

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Abstract

A copper-catalyzed migratory oxidative-coupling reaction between nitrones and various ethers/amines exhibited high functional-group tolerance. Even in aqueous media, the reaction proceeded efficiently. For practical use of this catalysis, a unique sequential Huisgen cycloaddition was demonstrated. Mechanistic investigations revealed that the reaction proceeded through oxidative catalytic activation of ethers/amines to afford iminium/oxonium intermediates by concurrent dual one-electron abstractions by copper(II) and oxyl radicals.

Abstract

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