Hexafluoroisopropyl Sulfamate: A Useful Reagent for the Synthesis of Sulfamates and Sulfamides
Matthew A. Sguazzin, Jarrod W. Johnson, Jakob Magolan
Abstract
Sulfamates and sulfamides are most often synthesized from alcohols and amines with sulfamoyl chloride, which is an unstable reagent. We have identified hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcohols, amines, phenols, and anilines under mild reaction conditions. The sole byproduct of the reaction is hexafluoroisopropanol (HFIP) and reaction products can often be isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation.
Topics & Concepts
ChemistryReagentPhenolsOrganic chemistryChlorideAqueous solutionReaction conditionsCombinatorial chemistryCatalysisSynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesEnzyme function and inhibition