Nickel-catalyzed hydrogenolysis of arenesulfonates using secondary alkyl Grignard reagents

Abstract

Neopentyl arenesulfonates react with secondary alkylmagnesium chlorides in the presence of dppfNiCl(2) to produce the corresponding arenes via the reductive cleavage of carbon-sulfur bond. Highest yield is obtained by using three equivalents of Grignard reagent to a mixture of arenesulfonate and dppfNiCl(2) in Et2O at room temperature. This reaction represents a novel method allowing the efficient hydrogenolysis of sulfur-containing groups in aromatic compounds.