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CF 3 SO 2 Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO 2 Insertion to Access Trifluoromethylated Cyclic N‐Sulfonylimines
Author(s) -
Li Zheng,
Jiao Lingcong,
Sun Yunhai,
He Zeying,
Wei Zhonglin,
Liao WeiWei
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001262
Subject(s) - trifluoromethylation , reagent , chemistry , bifunctional , electrochemistry , combinatorial chemistry , tandem , atom economy , medicinal chemistry , organic chemistry , catalysis , trifluoromethyl , materials science , electrode , composite material , alkyl
An unprecedented electrochemical trifluoromethylation/SO 2 insertion/cyclization process has been achieved in an undivided cell in an atom‐economic fashion. The protocol relies on tandem cyclization of N‐cyanamide alkenes by using Langlois’ reagent as a source of both CF 3 and SO 2 under direct anodically oxidative conditions, in which two C−C bonds, two C−X bonds (N−S and S−C), and two rings were formed in a single operation. This transformation enabled efficient construction of various trifluoromethylated cyclic N‐sulfonylimines from readily accessible materials.