Palladium-Catalyzed Amination of Diaryl Sulfoxides with Amides.

The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the amination reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reaction involves the activation of C-S and C-N bonds and the formation of a C-N bond with amides serving as amine surrogates. A broad range of sulfoxides and amides are compatible, furnishing substituted aniline in yields of up to 89%, and the protocol is scalable. Good regioselectivity was observed favoring the electron-deficient and less sterically hindered phenyl groups when unsymmetrical diphenyl sulfoxides were employed.