Issue 21, 2022

Electrochemical cyclization of N-cyanamide alkenes with CF3SO2Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds

Abstract

An electrochemical (bis)trifluoromethylative cyclization of N-cyanamide alkenes and alkynes is described, in which commercially available CF3SO2Na and readily available starting materials engaged in a novel electrochemical and sustainable process to assemble (bis)-C,N-trifluoromethylated cyclic amidines, which were previously inaccessible using known methods, with selective multiple bond formations in an undivided cell. Furthermore, this protocol also provided a rapid access to trifluoromethylated azines and amides in a controllable manner. A preliminary mechanism investigation and density functional theory (DFT) calculations were performed which revealed the possible reaction pathway.

Graphical abstract: Electrochemical cyclization of N-cyanamide alkenes with CF3SO2Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds

Supplementary files

Article information

Article type
Research Article
Submitted
17 Aug 2022
Accepted
09 Sep 2022
First published
14 Sep 2022

Org. Chem. Front., 2022,9, 5912-5920

Electrochemical cyclization of N-cyanamide alkenes with CF3SO2Na to access C,N-(bis)trifluoromethylated cyclic amidines and related compounds

Z. Yan, W. Li, Y. Wu, Q. Yan, Z. Wei and W. Liao, Org. Chem. Front., 2022, 9, 5912 DOI: 10.1039/D2QO01323A

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