Efficient synthesis of N-(trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride – the key agent in the preparation of compounds with superstrong electron-withdrawing groups and strong acidic properties

Abstract

N-(Trifluoromethylsulfonyl)trifluoromethanesulfonimidoyl fluoride 4 was prepared by the oxidative fluorination of N-(trifluoromethylsulfinyl)trifluoromethanesulfonamides 3a,b which are formed by the reaction of trifluoromethyltrimethylsilane with N-(sulfinyl)trifluoromethanesulfonamide in the presence of fluoride ions. Addition of MF to N-(sulfinyl)trifluoromethanesulfonamides affords the stable N-(fluorosulfinyl)trifluoromethanesulfonamides 2a,b. Reaction of 4 with N-nucleophiles readily forms the corresponding amides 6–8.