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Comprehensive Summary: A general and straightforward strategy for the synthesis of thioester‐substituted oxindoles via a palladium‐catalyzed thiocarbonylative cyclization process has been developed. With sulfonyl chlorides as promising sulfur source, a wide range of thioester‐substituted oxindoles were obtained in moderate to high yields. Both aryl and alkyl sulfonyl chlorides were well tolerated, and Mo(CO)6 played a dual role as both a CO source and a reductant in this approach. [ABSTRACT FROM AUTHOR]