Electrochemical aminotrifluoromethylation of unactivated alkenes with Langlois' reagent as the CF source

• Published in: New journal of chemistry 2024-01, Vol.48 (5), p.2183-2187
• Main Authors: An, Tongshun, Qin, Xiaowen, Liu, Chenwei, Yuan, Weiheng, Song, Tanyu, Yin, Zhiping
• Format: Article
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d3nj04705a

The straightforward synthesis of trifluoromethylated N-heterocycles from readily available amines has attracted significant interest from the academic community. Herein, we established a general and sustainable electrochemical approach for synthesizing various trifluoromethylated pyrrolidines. By utilizing the inexpensive and easily accessible Langlois' reagent as the source of CF 3 , a broad range of unactivated alkenes was transformed into corresponding heterocycles through a trifluoromethylation/cyclization cascade process in 43-80% yields. Mechanistic investigations indicated that this reaction may be initiated with the formation of a CF 3 radical through anodic single-electron transfer oxidation. The great benefit of this protocol is avoiding the use of metal catalysts and oxidants. More importantly, the late-stage modification of celecoxib and large-scale synthesis have revealed exceptionally beneficial and potential applications of the present method. An electrochemical approach for synthesizing various trifluoromethylated pyrrolidines was developed by utilizing Langlois' reagent as the CF 3 source, and different unactivated alkenes can be converted to the corresponding heterocycles in 43-80% yields.