Palladium-Catalyzed Carbonylative α-Arylation of 2-Oxindoles with (Hetero)aryl Bromides: Efficient and Complementary Approach to 3-Acyl-2-oxindoles

摘要

An efficient Pd-catalyzed carbonylative a-arylation of 2-oxindoles with aryl and heteroaryl bromides for the one-step synthesis of 3-acyl-2-oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the more common oxindole forming reactions. The transformation only requires a mild base and provides good to. excellent yields even with heteroaromatic substrates. Employing a near stoichiometric amount of ~(13)COgen, the methodology was easily extended to ~913)C acyl labeling. The general applicability of the reaction conditions was demonstrated in the synthesis of a structure related to the pharmaceutically active 3-acyl-2-oxindoles, tenidap.