Sulfonyl transfer mechanism in C–S coupling of phenylmagnesium bromide with phenyl arenesulfonates

The kinetics of C–S coupling of phenylmagnesium bromide with phenyl arenesulfonates has been studied in THF:toluene (7:10) at 90 °C. Kinetic data and Hammett relationship are consistent with an asynchronous SNa mechanism in which rate determining thiophilic attack of carbanion takes place much ahead of phenoxy group departure.

The kinetics of C–S coupling of phenylmagnesium bromide with phenyl arenesulfonates has been studied in THF:toluene (7:10) at 90 °C. Kinetic data and Hammett relationship are consistent with an asynchronous SNa mechanism in which rate determining thiophilic attack of carbanion takes place much ahead of phenoxy group departure.Figure optionsDownload as PowerPoint slide