A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylselanyl)but-1-yne via Palladium-Catalyzed Silylstannylation and Selenoxide Elimination

Abstract

The palladium-catalyzed silylstannylation of 4-(phenylselanyl)but-1-yne proceeded regio- and stereoselectively, followed by selenoxide elimination via oxidation to give (Z)-1-(trimethylsilyl)-2-(tributylstannyl)buta-1,3-diene in good yield. This conjugated diene underwent the Stille coupling reaction with various aryl iodides in the presence of Pd(PPh3)4 to afford (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes with high stereoselectivity. Reversing the order of selenoxide elimination and Stille coupling reaction in the synthetic procedure also resulted in good yields of (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes.