Lewis Acid-Catalyzed Sulfur Fluoride Exchange

Abstract

A new method uses metal Lewis acids as catalysts to convert sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides with silyl amines into S−N bond-containing compounds via sulfur fluoride exchange. The reaction successfully employs Ca(NTf 2 ) 2 as a catalyst to form sulfonamides, sulfamates, and sulfamides using in situ-generated or commercially available silyl amines in 35−99% yields. Other metal Lewis acids are also demonstrated to be catalysts in SuFEx, forming sulfonamides and sulfamates in yields comparable to those of Ca(NTf 2 ) 2 .Letter pubs.acs.org/OrgLett