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.