Pd(II)-Catalyzed Direct Dehydrogenative Mono- and Diolefination of Selenophenes

Pd(II)-catalyzed dehydrogenative Heck olefination of selenophenes with a broad olefinic substrate scope and high functional group tolerance is demonstrated. Carbonyl-substituted and phenyl-substituted olefins with electron-donating (D) and electron-accepting (A) groups can be regioselectively installed at C2 of the selenophene. The 2-olefinated selenophenes can subsequently undergo a second oxidative olefination to rapidly produce a new class of symmetrical D-pi-D or unsymmetrical D-pi-A 2,5-diolefinated selenophene materials.