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Visible‐Light‐Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Tien Tan Bui, Văn Hiếu Trần, Hee‐Kwon Kim

2021Advanced Synthesis & Catalysis27 citationsDOI

Abstract

Abstract Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange‐based “click chemistry.” Herein, a visible‐light‐mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K 2 S 2 O 5 and N ‐fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible‐light‐mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. magnified image

Topics & Concepts

SulfonylChemistryFluorideSulfurCombinatorial chemistryOrganic chemistryInorganic chemistryAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsFluorine in Organic Chemistry