Unprecedented palladium-catalyzed cross-coupling reaction of alpha-bromo sulfoxides with boronic acids

Org Lett. 2003 May 15;5(10):1705-8. doi: 10.1021/ol034358m.

Abstract

[reaction: see text] A new Suzuki-type palladium-catalyzed reaction of boronic acids with alpha-bromo sulfoxides has been developed using a protocol similar to the well-documented reaction of boronic acids with aryl halides. Both cross-coupling and homocoupling processes were observed. The best yields in cross-coupling products were obtained when the presence of oxygen was carefully excluded using degassed solvents. The oxidative addition palladium complex intermediate could be isolated and characterized by X-ray single-crystal diffraction.