Synthetic Applications of Monofluoromethylsulfonium Salts

Abstract

Monofluoromethylsulfonium salts are emerging reagents for the fluoromethylation and fluoromethylenation or fluorometyhlene transfer. This type of reagents display simple approach for introduction of fluoromethyl group into wide range of nucleophiles upon mild basic conditions. Recently, fluoromethylsulfonium salts have been demonstrated to act as a synthetic equivalent of otherwise challenging fluoromethylene synthon. For instance, these reagents can be used for the direct synthesis of monofluoroepoxides and fluorocyclopropanes from activated alkenes via sulfur fluoromethylide intermediate. Sulfonium salts are an alternative, easy-to-handle option to volatile and environmentally concerning freons for achieving monofluorinated compounds. This review focuses on synthetic application of these reagents known to date.