Synthesis of substituted oxindoles from alpha-chloroacetanilides via palladium-catalyzed C[bond]H functionalization.
A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, alpha-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed.
D000083:Acetanilides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D007700:Kinetics; D010165:Palladium / Q000737:chemistry
D000083:Acetanilides; D006843:Hydrocarbons, Chlorinated; D007211:Indoles; D010165:Palladium