title: Functional-group-tolerant catalytic migratory oxidative coupling of nitrones.
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.
authors: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors: Shogo
authors: S
authors: Hashizume
authors: Kounosuke
authors: K
authors: Oisaki
authors: Motomu
authors: M
authors: Kanai
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004987:Ethers / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000588:Amines; D004987:Ethers; D009589:Nitrogen Oxides; C015388:nitrones; D003300:Copper