CF<sub>3</sub>SO<sub>2</sub>Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO<sub>2</sub> Insertion to Access Trifluoromethylated Cyclic N‐Sulfonylimines
Zheng Li, Lingcong Jiao, Yun-Hai Sun, Zeying He, Zhonglin Wei, Wei‐Wei Liao
Abstract
Abstract 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.
Topics & Concepts
TrifluoromethylationReagentChemistryBifunctionalElectrochemistryCombinatorial chemistryTandemAtom economyMedicinal chemistryOrganic chemistryCatalysisPhysical chemistryTrifluoromethylMaterials scienceComposite materialAlkylElectrodeFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions