4-(Acetylamino)phenyl]imidodisulfuryl difluoride, AISF

Sulfofluorination reagent, CAS [2172794-56-6]

4-(Acetylamino)phenyl]imidodisulfuryl difluoride, schema

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.