title: Catalytic migratory oxidative coupling of nitrones.
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(sp(3))-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 carbocation is a key step.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Tokyo 113-0033, Japan.
authors.forename: Shogo
authors.initials: S
authors.lastname: Hashizume
authors.forename: Kounosuke
authors.initials: K
authors.lastname: Oisaki
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D007454:Iodides; D009589:Nitrogen Oxides; C015388:nitrones; D003300:Copper; C073870:cuprous iodide