Copper-Catalyzed Regio- and Stereoselective Hydroarylation of Ynamide.

Abstract

Presented herein is a copper-catalyzed trans-hydroarylation of ynamides. The reaction showcases the assembly of boronic acids across the carbon-carbon triple bond of ynamides. The reaction proceeds under mild conditions offering a complementary approach for the versatile synthesis of multifunctional (E)-α,β-disubstituted enamides. Moreover, the hydroarylation process is highly regio- and stereoselective. The transformation shows a broad scope (30 examples) and tolerates a wide range of labile functional groups. Control experiments provide substantive evidence supporting the mechanistic cycle and the observed selectivity.