A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes

Abstract

Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an <i>in situ</i>-generated and geometrically pure vinyl-Cu(I) species to form the <i>Z</i>,<i>Z</i>- or <i>Z</i>,<i>E</i>-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted <i>Z</i>-dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches.