Catalytic Activation of C−H and C−C Bonds of Allylamines via Olefin Isomerization by Transition Metal Complexes

Abstract

The metal-catalyzed reaction of olefins with allylamines bearing coordination sites (2-pyridyl groups) was studied. With Ru3(CO)12 as catalyst, activation of C−H bonds led to the formation of ketimines that were hydrolyzed to give asymmetric ketones. With [(C8H14)2RhCl]2, both C−H and C−C bonds were activated and symmetric ketones were formed on hydrolysis. The reaction involves double bond migration of the allylamine to form an aldimine.