Convenient Synthesis of Thioester‐Substituted Oxindoles by Palladium‐Catalyzed Thiocarbonylative Cyclization with Sulfonyl Chlorides as the Sulfur Source

• Published in: Chinese journal of chemistry Vol. 41; no. 2; pp. 188 - 192
• Main Authors: Xu, Ren‐Rui, Fang, Xiuyu, Qi, Xinxin, Wu, Xiao‐Feng
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 15.01.2023; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkene; Carbonylation; Chemistry; Chemistry, Multidisciplinary; Chlorides; Oxindoles; Palladium; Physical Sciences; Reducing agents; Science & Technology; Substitutes; Sulfonyl Chlorides; Sulfur; Synthetic methods; Thiocarbonylation; Thioesters; Oxindoles; Sulfonyl Chlorides; CARBONYLATION REACTIONS; SCOPE; Palladium; THIOL ESTERS; ALDEHYDES; Thiocarbonylation; PARAMETERS; Carbonylation; Alkene; KETONE SYNTHESIS; Synthetic methods; ARYL; BOND; DERIVATIVES
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202200530

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. A general and straightforward strategy for the synthesis of thioester‐substituted oxindoles via a palladium‐catalyzed thiocarbonylative cyclization process has been developed. With both aryl and alkyl sulfonyl chlorides as promising sulfur source, a wide range of thioester‐substituted oxindoles were obtained in moderate to high yields.