Organocatalytic SuFEx click reactions of SO2F2.

Abstract

An organocatalytic method for the SuFEx click reaction of gaseous SO₂F₂ is described. Different organic bases such as DBU, TBD, triethylamine and Hünig's base can efficiently catalyze the SuFEx of SO₂F₂ with various phenols to produce aryl fluorosulfates in 61-97% yields. Under the same conditions, pyridone, pyrazolone and amines can also react with SO₂F₂ to afford the corresponding heteroaryl fluorosulfates or sulfamoyl fluorides in good yields. In this process, molecular sieves absorb the acidic HF efficiently, avoiding the use of stoichiometric amounts of organosilicon reagents and excess bases.