Perfluoroalkylations of carbanions with (perfluoroalkyl)-phenyliodonium triflates (FITS reagents).
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FITS reagents reacted with primary alkylmagnesium halides in THF at −78 °C to give the corresponding perfluoroalkyl(R<SUB>f</SUB>)-alkanes in moderate to good yields. But an alkyl-lithium or -copper gave a poor yield of the R<SUB>f</SUB>-product. The reaction of FITS with secondary or tertiary alkylmagnesium halides resulted in low yields of the products. Alkynyl-lithiums or -magnesium halides produced R<SUB>f</SUB>-alkynes in favorable yields. The reaction with aryl or vinylmagnesium halide was complex and the yields of R<SUB>f</SUB> derivatives were low. FITS also reacted smoothly with enolate anions of active methylene compounds such as 2-methyl-1,3-cyclopentanedione, ethyl 2-methylacetoacetate, and ethyl 2-oxocyclopentanecarboxylate in a polar solvent to afford <I>O</I>- and <I>C</I>-perfluoroalkylation products in moderate yields, ratios <I>O</I>-/<I>C</I>-Rf products depending on the reaction temperature. Anions of diethyl 2-methylmalonate and 2-nitropropane afforded <I>C</I>-R<SUB>f</SUB>-compounds only.
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