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Synlett 2022; 33(05): 401-408
DOI: 10.1055/a-1700-6453
DOI: 10.1055/a-1700-6453
synpacts
Radical Fluorosulfonylation: Accessing Alkenylsulfonyl Fluorides from Alkenes and Alkynes
The National Natural Science Foundation of China (21602028), the Recruitment Program of Global Experts, the Beijing National Laboratory for Molecular Sciences (BNLMS201913), and Fuzhou University are gratefully acknowledged for their financial support.
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
Publication History
Received: 05 November 2021
Accepted after revision: 18 November 2021
Accepted Manuscript online:
18 November 2021
Article published online:
17 December 2021
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