Journal of the American Chemical Society 2012-12-26

Palladium-catalyzed vinylation of aminals with simple alkenes: a new strategy to construct allylamines.

Yinjun Xie, Jianhua Hu, Yanyu Wang, Chungu Xia, Hanmin Huang

Index: J. Am. Chem. Soc. 134(51) , 20613-6, (2012)

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Abstract

A novel, highly selective palladium-catalyzed vinylation reaction for the direct synthesis of allylic amines from styrenes and aminals has been established. The utility of this method was also demonstrated by the rapid synthesis of cinnarizine from aldehydes, amines, and simple alkenes in one-pot manner. Mechanistic studies suggested that the reaction proceeds through a valuable cyclometalated Pd(II) complex generated by the oxidative addition of aminal to a Pd(0) species.