Nucleophilic Ortho 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.