Perfluoroallylation of Alkenes with Perfluoroallyl Iodide Catalyzed by Copper

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Abstract
The addition of perfluoroallyl iodide to alkenes is induced by copper powder (10-20 mol %) in the absence of solvent at 50 °C to give the corresponding adducts in good yield. A variety of functional groups such as trimethylsilyl, ketone, epoxy, ester and phosphonate in the alkenes do not interfere with the addition reaction. With dienes, the bis(perfluoroallyl) products are obtained when two equivalents of perfluoroallyl iodide are used. Reduction of the adducts with zinc in the presence of nickel dichloride in moist tetrahydrofuran affords iodine-free perfluoroallyl derivatives.
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