Catalytic Migratory Oxidative Coupling of Nitrones

S Hashizume, K Oisaki, M Kanai

Index: Hashizume, Shogo; Oisaki, Kounosuke; Kanai, Motomu Organic Letters, 2011 , vol. 13, # 16 p. 4288 - 4291

Full Text: HTML

Citation Number: 22

Abstract

A Cu (I)-catalyzed migratory oxidative coupling between nitrones and heterocycles or a methylamine is described. Selective C–C bond-formation proceeds through cleavage of two C (sp3)–H bonds concomitant with C N double bond-migration. The reaction provides an alternating nitrone moiety, allowing for further synthetically useful transformations. Radical clock studies suggest that the nucleophilic addition of nitrones to an oxidatively generated ...