Palladium-catalyzed C-H functionalization of N-arylpropiolamides with aryliodonium salts: selective synthesis of 3-(1-arylmethylene)oxindoles.

A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)2 and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.