Synthesis of Sulfonyl Fluorides Using Direct Chloride/Fluoride Exchange in Potassium Fluoride and Water/Acetone

J Org Chem. 2023 Apr 7;88(7):4761-4764. doi: 10.1021/acs.joc.2c02630. Epub 2023 Mar 15.

Abstract

A multitude of synthetic routes are available for the preparation of sulfonyl fluorides (R-SO2F) whose discovery is now almost a century old. These syntheses are often limited by the scope, hazardous materials, and elaborate procedures. The simple and mild procedure based on direct chloride/fluoride exchange from a sulfonyl chloride (R-SO2Cl) starting material in a KF and water/acetone biphasic mixture is investigated. Seventeen examples in high yield (84-100%) with wide scope are described.