Perfluorobutanesulfonyl fluoride

NfF serves as an entry point to nonafluorobutanesulfonates (nonaflates), which are valuable as electrophiles in palladium catalyzed cross coupling reactions.

Their resistance to hydrolysis makes nonaflates superior electrophiles in Buchwald-Hartwig couplings, where this side reaction can be deleterious to yields of the desired product.

[5] Simple aldehydes and ketones react with NfF in the presence of bases such as DBU or phosphazenes to give alkenyl nonaflates in high yields without formation of a discrete enolate.

[6] Trimethylsilyl enol ethers react with NfF in the presence of a substoichiometric fluoride source at 0 °C to ambient temperature to give alkenyl nonaflates in moderate to good yields.

It has recently been discovered that upon reaction of NfF with alcohols to generate alkyl nonaflate, the released F− can be used to activate trimethylsilyl-bound nucleophiles in situ to produce several deoxy-diversified products.

[10] NfF reacts with ammonium chloride in the presence of triethylamine in acetonitrile to give the triethylammonium salt of the superacidic bis-nonafluorobutanesulfonimide in 97% yield.