Abstract
Monofluoromethylsulfonium salts are emerging reagents for the fluoromethylation and
fluoromethylenation or fluoromethylene transfer. Using this type of reagent is a simple
approach for the introduction of the fluoromethyl group into a wide range of nucleophiles
using mild basic conditions. Recently, fluoromethylsulfonium salts have been demonstrated
to act as a synthetic equivalent for the challenging fluoromethylene synthon. For
instance, these reagents can be used for the direct synthesis of monofluoroepoxides
and fluorocyclopropanes from activated alkenes via a 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.
1 Introduction
2 Fluoromethylation of O-, N-, S-, P-, and C-Nucleophiles
3 Sulfonium Salts for Radical Monofluoromethylation of Alkenes
4 Sulfonium Salts for Fluoromethylene Transfer
5 Conclusions
Key words
fluoromethylation - fluoromethylenation - sulfur fluoromethylide - sulfonium salts
- fluorocarbene - fluoromethylene transfer
