Aminofluorosulfonylation of <i>β,γ</i>-Unsaturated Hydrazones with Sulfur Dioxide and <i>N</i>-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides
Zhi-Min Yan, Qi Lin, Tong-Yang Cao, Jiali Liu, Huijie Du, Yichen Dong, Wei Li, Lijin Wang
Abstract
An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ -unsaturated hydrazones with sulfur dioxide and NFSI as the starting materials under mild conditions. The sulfonyl fluoride products could be successfully transformed into the corresponding sulfonate esters and amides via the sulfur(VI) fluoride exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that the reaction operates through a radical cyclization/SO 2 insertion/fluorination cascade process.
Topics & Concepts
SulfonylChemistrySulfurFluorideSulfonatePyrazolineFluorineOrganic chemistrySulfur dioxideInorganic chemistrySodiumAlkylSulfur-Based Synthesis TechniquesFluorine in Organic ChemistryClick Chemistry and Applications