Nucleophilic <i>Ortho</i> Allylation of Aryl and Heteroaryl Sulfoxides

Aryl and heteroaryl sulfoxides undergo ortho allylation upon treatment with Tf2O and allylsilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods including Kumada–Corriu cross-coupling of the organosulfanyl group.