Syntheses utilizing n-perfluoroalkyl iodides [RFI, CnF2n+1-I] 2000–2010

This review presents a comprehensive assessment of the synthetic utility of n-perfluoroalkyl iodides (RFI, CnF2n+1-I, where n = 2–14) in the published literature from 2000 through 2010. RFI is a versatile synthetic reagent widely utilized to introduce the perfluoroalkyl functionality and its unique functional characteristics into organic substances. Two distinct analysis tools were employed. First, Reaxys® was employed to examine the versatility and occurrences of RFI in 1356 non-polymeric synthetic transformations. The most common RFI synthetic conversions were (i) free-radical addition to carbon–carbon double or triple bonds, (ii) coupling to aryl halides, and (iii) Grignard, organolithium, or similar RF anion addition to ketones and aldehydes. RFI were also used as a chain transfer reagent in free-radical polymerization reactions of fluorinated and other unsaturated monomers. Second, a complementary Chemical Abstracts’ STN AnaVist® search was employed to summarize the 779 publications describing reaction products that contained n-perfluoroalkyl chains (CnF2n+1-, where n = 2–4). The most common uses for materials into which RFI was incorporated were surfactants, pesticides, electronic materials, pharmaceuticals, liquid crystals, dyes and optical materials, battery electrolytes, repellents, lubricants and polymerization catalysts.