Palladium-Catalyzed C-H Arylation of alpha,beta-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives

摘要

A unique chemo- and regioselective alpha- and gamma-arylation of palladium azapentadienyl intermediates is presented. Two distinct catalysts and sets of conditions successfully controlled the regioselectivity of the arylation. These methods provide the first umpolung C-H functionalization of azapentadienyl palladium intermediates and enable the divergent synthesis of allylic amine and enamine derivatives, which are of significant interest in the pharmaceutical industry.