N-Heterocyclic carbene-catalyzed silicon-free sulfur fluoride exchange reactions of sulfonimidoyl fluorides

As the monoaza analogous of sulfonates and sulfonamides, sulfonimidate ester and sulfonimidamide have attracted growing attention in recent years. In this paper. We report an organocatalytic silicon-free sulfur fluoride exchange (SuFEx) reaction of sulfonimidoyl fluorides for the synthesis of these valuable organosulfurs. Under the catalysis of 10 mol% N-heterocyclic carbene (NHC), and MS 4Å, sulfonimidoyl fluorides reacted with phenols to produce sulfonimidate esters in 55-99% yields. In addition, under the relay catalysis of 10 mol% NHC and HOBt, various amines coupled with sulfonimidoyl fluorides to give sulfonimidamides in 55-99% yields.