1-(Fluorosulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (desmethyl SuFEx-IT) is a bench-stable fluorosulfurylation reagent used as a safer alternative to toxic sulfuryl fluoride (SO2F2) gas1,2. It efficiently introduces FO2)S+ groups in SuFEx (Sulfur(VI) Fluoride Exchange) reactions. The reagent enables selective fluorosulfurylation of phenols and amines, forming fluorosulfates and sulfamoyl fluorides. It is widely applied in click chemistry, bioconjugation, and pharmaceutical synthesis. Unlike gaseous SO2F2, this solid reagent is scalable, easy to handle, and cost-effective. It remains stable at room temperature or under refrigeration, making it a practical tool for fluorosulfurylation reactions.
Synonyms: 3-methylimidazol-3-ium-1-sulfonyl fluoride, trifluoromethanesulfonate; 1-(fluorosulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate; desmethyl SuFEx-IT
A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO2+” Donor of Unprecedented Reactivity, Selectivity, and Scope.
Guo T.; Meng G.; Zhan X.; Yang Q.; Ma T.; Xu L.; Sharpless K. B.; Dong J. Angewandte Chemie - International Edition 2018, 57 (10), 2605–2610. DOI: 10.1002/anie.201712429
Desmethyl SuFEx-IT: SO2F2-Free Synthesis and Evaluation as a Fluorosulfurylating Agent.
Bertram J.; Neumaier F.; Zlatopolskiy B. D.; Neumaier B. Journal of Organic Chemistry 2024, 89 (6), 3821–3833. DOI: 10.1021/acs.joc.3c02643
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