Efficient stereochemical controllers in biaryl Suzuki coupling reactions: benzylic carbinols bearing in beta-position thioether, dimethylamino, or sulfoxide groups.

Highly atropo-diastereoselective Suzuki coupling between aryl halides bearing stereogenic benzylic carbinols with sulfoxide, thioether, or dimethylamino groups as efficient internal chelating ligands and 2-methoxy-1-naphthylboronic acid were performed with high yields; a palladacycle is proposed as a potential transition state. [reaction: see text]