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

Abstract

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.