Silyl Cyanopalladate-Catalyzed Friedel–Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

Abstract 3-Aryloxindole derivatives were synthesized through a Friedel–Crafts-type cyclization. The reaction was catalyzed by trimethylsilyl tricyanopalladate complex generated in situ from cyanide and Pd(OAc)2. Wide varieties of diethyl phosphates derived N-arylmandelamides converted almost quantitatively into oxindoles. When N,N-dibenzylamide used instead an anilide substrate, benzo-fused δ-lactam obtained. An oxindole product subjected to substitution reactions afford 3,3-diaryloxindoles with two different aryl groups.