TMSN3 Initiated Electrochemical Mono-Dealkylation of Tertiary Amides

• Published in: Journal of organic chemistry 2024-12
• Main Authors: Ding, Anjun, Liu, Meixia, Jiang, Yunxiang, Liu, Xiaoyong, Yang, Junpeng, Liu, Wen, Fu, Zhengjiang, Guo, Shengmei, Cai, Hu
• Format: Article
• Language: English
• ISSN: 1520-6904; 1520-6904
• DOI: 10.1021/acs.joc.4c01813

N-Dealkylation of amides is a general process in living organisms and organic synthetic chemistry, but an efficient chemical approach for this transformation has not been explored. Herein, we report an electrochemical method for the monodealkylation of a wide range of tertiary amides, including benzamides, alkyl amides, lactams, and sulfonamides. The reaction proceeds smoothly under mild conditions using TMSN3 as the initiator and is not limited to deethylation or demethylation. This protocol enables the large synthesis, providing a valuable tool for synthetic organic chemistry.N-Dealkylation of amides is a general process in living organisms and organic synthetic chemistry, but an efficient chemical approach for this transformation has not been explored. Herein, we report an electrochemical method for the monodealkylation of a wide range of tertiary amides, including benzamides, alkyl amides, lactams, and sulfonamides. The reaction proceeds smoothly under mild conditions using TMSN3 as the initiator and is not limited to deethylation or demethylation. This protocol enables the large synthesis, providing a valuable tool for synthetic organic chemistry.