Nickel-catalyzed addition of benzenethiol to alkynes: Formation of carbon-sulfur and carbon-carbon bonds

Abstract

Nickel-catalyzed addition of benzenethiol to alkynes leads to alkenyl and dienyl sulfides; the direction of the process can be controlled by varying the PhSH/alkyne ratio. An advanced procedure, which ensures higher yields of 2-phenylsulfanylalkenes, includes gradual addition of alkyne to the other reactants. The structures of conjugated dienyl sulfides formed in the reaction were determined by 2D NMR spectroscopy. © 2006 Springer Science+Business Media, Inc.