Fluoromethylene Transfer from Diarylfluoromethylsulfonium Salts: Synthesis of Fluorinated Epoxides

Abstract

Diarylfluoromethyl sulfonium salts are efficient fluoromethylene transfer reagents equivalent to fluorocarbene, which is difficult to access. This was demonstrated by the development of a monofluorinated Johnson-Corey-Chaykovsky reaction with ketones and aldehydes, delivering uncommon 2-unsubstituted fluoroepoxides. This is the first evidence for the feasibility of sulfur fluoromethylylide and its action as a reaction intermediate.

Keywords: Johnson-Corey-Chaykovsky reaction; fluorinated epoxides; fluoromethylenation; fluorooxiranes; sulfur fluoromethylylide.