Nonafluorobutanesulfonyl fluoride (PBSF) is a colorless volatile liquid, immiscible with water but soluble in common organic solvents. Its structural properties are similar to those of perfluorooctyl sulfonyl fluoride.
It is liquid at room temperature, immiscible with water, but soluble in common organic solvents.
As an entry point for nonafluorobutane, PBSF is very valuable as an electrophile for palladium-catalyzed cross-coupling reactions. Compared with the more commonly used trifluoromethanesulfonic anhydride as a perfluoroalkyl sulfonating agent, Nonafluorobutanesulfonyl fluoride has the advantages of lower cost and higher stability.
Through a multi-dimensional comparative study, it was found that PBSF is very suitable for the deoxyfluorination reaction with cycloalkyl alcohols. At the same time, the effect of PBSF is also closely related to the steric hindrance of alkali.
The fluoride leaving group is easily replaced by nucleophiles (such as amines, phenates and enolates) to generate sulfonamides, aryl nonanoates and alkenyl nonanoates, respectively.
Nonafluorobutanesulfonyl fluoride is made by the electrochemical fluorination of sulfolane. It is mainly used in the synthesis of fluorocarbon surfactants, fluorinated pesticides, dyes, and polycarbonate processing dispersants.