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Functional‐Group‐Tolerant Catalytic Migratory Oxidative Coupling of Nitrones
Authors:Shogo Hashizume  Dr Kounosuke Oisaki  Prof?Dr Motomu Kanai
Institution: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)
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.
Keywords:C?C bond formation  C?H activation  copper  cycloaddition  nitrones
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