A stereospecific route to olefins through sequential coupling reaction of Grignard reagents with 1-bromo-2-phenylthioethene in the presence of nickel or palladium catalysts

Abstract

The room temperature sequential formation of two C–C bonds by reaction of aromatic or aliphatic Grignard reagents with (E)- or (Z)-1-bromo-2-phenylthioethene in the presence of nickel(II) or palladium(II) catalysts provides a novel stereospecific route to a variety of (E)- or (Z)-olefins of the R–CHCH–R and R¹–CHCH–R² type, with a stereoselectivity higher than 99% for the (E) isomers and in the range 95–98% or the (Z) isomers.