Unlike the polar RF-COOH or RF-SO3H perfluoroalkyl surfactants, the less polar RF-X (X = Cl, Br, I) derivatives are of much less environmental concern and remain significant building blocks in organic, organometallic, pharmaceutical and polymer chemistry. However, their synthesis is non-trivial, and follows dissimilar pathways without common intermediates which results in a commercial offering skewed towards Cl &gt;&gt; Br &gt;&gt; I. By contrast, the more reactive RF-I derivatives remain the most desirable. However, the strongly deactivating fluorines effectively block substitutions, and classic NaI/acetone RF-Cl to RF-I SN2 interconversions are not feasible. We are currently exploring new metal-mediated catalytic methods for such derivatizations towards novel RF-I initiators for iodine degenerative transfer (IDT) controlled radical polymerizations of fluorinated monomers. This presentation will describe an in-depth study of the effect of reaction variables (metal, ligand, solvent, temperature, light etc.) on the mechanism and yield of such transformations, and applications in the IDT of vinylidene fluoride.

Metal mediated derivatization of deactivated fluoroalkyl halides towards polymerization initiators

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ACS Spring 2023

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