Synthesis and reactions of perfluoroalkylene-bridged bis(hypervalent iodine) reagents

Abstract

We report the synthesis and reactivity of a novel bis(hypervalent iodine) reagent incorporating a perfluoroalkylene chain. This reagent was readily synthesized in two steps from commercially available α,ω-dibromoperfluoroalkanes, and fully characterized by NMR spectroscopy and high-resolution mass spectrometry. Furthermore, we demonstrated that the reagent reacts with various alkenes and nucleophiles in the presence of a copper(I) catalyst, enabling efficient three-component transformations at both termini of the perfluoroalkylene chain under mild conditions. This methodology provides a new and efficient strategy for incorporating of perfluoroalkylene chains into organic molecules.