The chemistry of polyfluorinated azides
In 2017, we reported a breakthrough in azide chemistry. CF3N3 and longer carbon chain analogues were prepared from silanes or other carbanion precursors, which opened a door to study properties and reactivity of these compounds. They are no longer regarded as chemical curiosities. Furthermore, they were shown to be stable (not explosive) and readily undergo copper(I)-catalyzed azide-alkyne cycyloaddition (CuAAC) to form novel N-perfluoroalkyl triazoles (Angewandte Chemie International Edition 56: 346-349, 2017). Other tetrafluoroethylene and tetrafluoroethyl azides and triazoles were reported (Organic and Biomolecular Chemistry 15: 4962-4965, 2017).
Transannulation reaction of N-(per)fluoroalkyl triazoles provided novel N-(per)fluoroalkyl pyrroles and imidazoles (Chemical Communications 54: 3258-3261, 2018).