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CFSO₂Na作为一种双功能试剂:烯烃的电化学三氟甲基化反应伴随SO₂插入以合成三氟甲基化环状N-磺酰亚胺。

CF SO Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines.

作者信息

Li Zheng, Jiao Lingcong, Sun Yunhai, He Zeying, Wei Zhonglin, Liao Wei-Wei

机构信息

Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, 130012, P. R. China.

出版信息

Angew Chem Int Ed Engl. 2020 Apr 27;59(18):7266-7270. doi: 10.1002/anie.202001262. Epub 2020 Mar 9.

Abstract

An unprecedented electrochemical trifluoromethylation/SO  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 and SO 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.

摘要

一种前所未有的电化学三氟甲基化/硫插入/环化过程已在无隔膜电解池中以原子经济的方式实现。该方法依赖于在直接阳极氧化条件下,使用朗格卢瓦试剂作为CF和SO的来源,对N-氰基酰胺烯烃进行串联环化反应,在一次操作中形成两个C-C键、两个C-X键(N-S和S-C)以及两个环。这种转化能够从易于获得的原料高效构建各种三氟甲基化的环状N-磺酰亚胺。

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