Fluoroalkyl iodonium salts

DesMarteau and coworkers reported the preparation, X-ray crystal structure and chemistry of trifluo-roethyliodonium salts 391 by the reaction of fluoroalkyliodo-bis(trifluoroacetates) 389 with benzene and triflimide acid (390) (Scheme 2.113) [68,531,532], The structure of trifluoroethyl(phenyl)iodonium salt 391 (n = 1) was established by a single-crystal X-ray analysis [68], In contrast to fluoroalkyliodonium triflates 383, compounds 391 are stable to water and can be used as reagents for fluoroalkylation reactions in aqueous media. 

Fluoroalkyl(aryl)iodonium salts are the most stable and practically important class of alkyl(aryl)iodonium derivatives. The application of such salts as electrophilic fiuoroalkylating reagents was reviewed in 1996 by Umemoto [1017]. Perfluoroalkyl(phenyl)iodonium trifiates (FITS reagents) 764 are efficient perfluoroalky-lating reagents toward various nucleophiUe substrates, sueh as arenes, carbanions, alkynes, alkenes, carbonyl compounds, amines, phosphines and sulfides [1017]. Scheme 3.300 shows several representative examples of electrophilic perfluoroalkylations using FITS reagents. 

Lu C, VanDerveer D, DesMarteau DD (2008) Fluoroalkylation of imidazoles by hypervalent iodonium salts. Org Lett 10 5565-5568... 

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