Abstract
Sulfonyl 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 Introduction
1.1 Functional Group Constructions
1.2 Modular Synthesis with FSO2-Containing Synthetic Blocks
1.3 Direct Fluorosulfonylation
2 Radical Fluorosulfonylation of Alkenes with FSO2Cl
3 Mechanistic Study
4 Radical Chloro/Fluorosulfonylation of Alkynes
5 Summary and Outlook
Key words
click chemistry - SuFEx - fluorosulfonylation - radical reactions - sulfonyl fluorides
