Abstract
Perfluoroalkyl iodide is a well-known source for the introduction of perfluoroalkyl groups into organic molecules. From a perfluoroalkyl iodide, a perfluoroalkyl radical is relatively easy to produce by one-electron reduction of the iodide. On the other hand, reports of the perfluoroalkylation of organic molecules with the iodide via a perfluoroalkyl cation are scarce due to the high electronegativity of fluorine. We would like to report here perfluoroalkylation of electron-rich compound via a cationic intermediate using various redox systems; perfluoroalkyl iodide is reduced to perfluoroalkyl radical, and the resulting radical reacts with an organic molecule to provide a new radical species which is successively oxidized to the corresponding cationic intermediate. By the choosing of the redox conditions, perfluoroalkylated styrenes and their related compounds were selectively synthesized from perfluoroalkyl iodide with styrenes. Perfluoroalkylated arenes were also achieved by the reaction of perfluoroalkyl iodide with various arenes via arenium radicals and then the cations.
