Aliphatic sulfonyl fluoride synthesis via reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acid NHPI esters

Based on a radical sulfur dioxide insertion and fluorination strategy, we have developed an efficient method for aliphatic sulfonyl fluoride synthesis using abundant carboxylic acids, a reductant, a sulfur dioxide surrogate and the electrophilic fluorination reagent N-fluorobenzenesulfonimide (NFSI) under reduction conditions. This protocol provides a convenient synthetic pathway for various aliphatic sulfonyl fluorides and tolerates a wide range of functional groups.

Automated summary

By utilizing a radical sulfur dioxide insertion and fluorination strategy, we have successfully developed an efficient method for synthesizing aliphatic sulfonyl fluorides. This method utilizes readily available carboxylic acids, a reductant, a sulfur dioxide surrogate, and the electrophilic fluorination reagent NFSI under reduction conditions. The protocol allows for the synthesis of various aliphatic sulfonyl fluorides and is compatible with a wide range of functional groups.