Synthesis of α-Arylated Allylsilanes through Palladium-Catalyzed γ-Selective Allyl−Aryl Coupling

Abstract

A palladium-catalyzed gamma-selective allyl-aryl coupling between gamma-silylated allylic esters and arylboronic acids produced alpha-arylated allylsilanes with E-alkene geometry. The reaction tolerated various functional groups in both the arylboronic acids and the allylic esters and afforded functionalized allylsilanes. The reaction of optically active allylic esters took place with excellent alpha-to-gamma chirality transfer with syn stereochemistry to give chiral allylsilanes.