AISF

CAS 2172794-56-6, Cat. No EN300-6745900

Sulfofluorination reagent

Fluorosulfates have a variety applications in organic synthesis acting like a pseudo-halogen in wide range of Pd-catalysed cross-coupling reactions. They are also used as tool compounds in proteomics. AISF is a stable under normal conditions but crystalline substance, soluble in THF used for sulfofluorination of phenols and amines. This reagent is good alternative to hazardous SO₂F₂ which possesses greater selectivity and much easier to handle than gaseous sulfuryl fluoride. The reaction happens at room temperature, and it takes minutes for sulfofluorination to happen on diverse scope of substrates. Moreover, great chemoselectivity observed, AISF may be used in presence of anilines, primary and secondary alcohols as well as carboxylic acids that leave unaffected.

Synonyms: 4-(Acetylamino)phenyl]imidodisulfuryl difluoride

Selected publication

1. Palladium in Cephalosporin Chemistry: An Inexpensive Triflate Replacement for Palladium Acetate Mediated Coupling Reactions.

Roth G. P.; Sapino C. Tetrahedron Lett 1991, 32 (33), 4073–4076. DOI: 10.1016/S0040-4039(00)79866-2

2. Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.

Chen W.; Dong J.; Plate L.; Mortenson D. E.; Brighty G. J.; Li S.; Liu Y. et al. J Am Chem Soc 2016, 138 (23), 7353–7364. DOI: 10.1021/jacs.6b02960

3. [4‐(Acetylamino)Phenyl]Imidodisulfuryl Difluoride.

Carneiro S. N.; Ball N. D.; Lee J.; Ende C. W. Encyclopedia of Reagents for Organic Synthesis 2021, 1–3. DOI: 10.1002/047084289X.rn02400

4. Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides.

Zhou H.; Mukherjee P.; Liu R.; Evrard E.; Wang D.; Humphrey J. M. al. Org Lett 2018, 20 (3), 812–815. DOI: 10.1021/acs.orglett.7b03950