Kinetics and mechanism of the C-S coupling reactions of aryl Grignard reagents with aryl arenesulfonates

Abstract

The kinetics of the C-S coupling of arylmagnesium bromides with phenyl tosylate has been studied in THF: toluene at 90°C. The reaction is first order in Grignard reagent and first order in phenyl tosylate. Kinetic data, Hammett relationship and activation parameters are consistent with a nucleophilic addition mechanism involving rate determining attack of carbanion to sulfonyl group followed by a fast phenoxide group leaving. © Versita Warsaw and Springer-Verlag Berlin Heidelberg 2008.