The degradation of perfluoroalkyl substances (PFAS) has been of particular interest environmentally, given their innate ability to accumulate in water sources and biota in the condensed phase and the high global warming potentials of gaseous compounds like CF4. Hydro- and alkylative defluorination (H/alkDF) utilizing silylium and alumenium cations, respectively, have been shown to selectively activate C(sp3)–F bonds found in the large majority of environmentally relevant PFAS. This chemistry formally replaces a C–F bond with a C–H or C–alkyl bond for HDF and alkDF respectively. A sufficiently weakly coordinating anion (WCA) is of paramount importance to unlock the desired activity of these main-group cations. We studied a variety of main-group precursors, weakly coordinating anions, and fluorinated substrates and will discuss the current limitations of the system and the design of new activators to target more challenging PFAS going forward.

Hydro- and alkylative defluorination (H/alkDF) of C(sp3)–F bonds with highly electrophilic main-group cations

ACS Spring Meeting 2021

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