Development of Perfluoroalkylation Based on the Ate Complex Chemistry

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The generation method of stable perfluoroalkylzinc reagents from perfluoroalkyl iodide using the combination of Me2Zn and LiCl has been developed. Although perfluoroalkyllithium and Gregnard reagents are unstable due to facile α- or β-metal fluoride (M-F) elimination, the perfluoroalkylzinc species thus obtained is stable and can be utilized at room temperature. Theoretical investigations have revealed the origin of the stability, compared to that of lithium reagents. This system is also applicable for the generation of perfluorophenylzinc species. The application to the nucleophilic perfluoroalkylation and perfluorophenylation has been demonstrated.