Radical Fluorosulfonylation: Accessing Alkenylsulfonyl Fluorides from Alkenes and Alkynes

Abstract

AbstractSulfonyl fluorides have widespread applications in many fields. In particular, the increasing research interest on the study of sulfonyl fluorides in the context of chemical biology and drug discovery in the past decade has raised a high demand for new and efficient methods for the synthesis of sulfonyl fluorides. Even though many synthetic routes have been developed in recent years, the corresponding radical fluorosulfonylation remains elusive. Here, we report our efforts toward this goal, and the identification of sulfuryl chlorofluoride (FSO2Cl) as an effective fluorosulfonyl radical precursor, as well as the development of radical fluorosulfonylation of alkenes and radical trans-chloro/fluorosulfonylation of alkynes.1 Introduction1.1 Functional Group Constructions1.2 Modular Synthesis with FSO2-Containing Synthetic Blocks1.3 Direct Fluorosulfonylation2 Radical Fluorosulfonylation of Alkenes with FSO2Cl3 Mechanistic Study4 Radical Chloro/Fluorosulfonylation of Alkynes5 Summary and Outlook