An Overview of the Reactions with Trifluoromethyl Trifluoromethanesulfonate

Synthesis of fluorine-containing compounds is greatly dependent upon the development and application of fluorinated reagents.Thanks to the unique fluorine effects, fluorinated reagents usually exhibit different properties and reaction profiles from those of the non-fluorinated analogues.Among various trifluoromethoxylation reagents, trifluoromethyl trifluoromethanesulfonate has drawn much attention in recent years because of its easy preparation, low cost and diverse reactivities.This reagent rapidly decomposes to form trifluoromethoxy anion in the presence of fluoride ion, thus regarded as a reservoir of trifluoromethoxy anion, and has been widely used in the nucleophilic trifluoromethoxylation reactions.Moreover, the trifluoromethoxy anion derived from trifluoromethyl trifluoromethanesulfonate and nucleophiles has poor thermal stability and tends to decompose at room temperature to afford fluorophosgene and fluorine anion, which can be used as a carbonylation reagent, a fluoroformylation reagent, a condensation agent or a nucleophilic fluorination reagent.The trifluoromethoxylation, carbonylation and fluorination reactions with trifluoromethyl trifluoromethanesulfonate as the reagent are reviewed.