The group of Dr. Petr Beier has reported the synthesis of trifluoromethyl azide from nucleophilic CF3SiMe3 and electrophilic azide sources. Previously unknown longer chain analogues are prepared using the same strategy. Importantly, perfluoroalkyl azides are not explosive and show no sign of decomposition at 150 °C. In contrast, short chain alkyl azides are avoided because of their explosive character. Perfluoroalkyl azides undergo fluorinated version of copper-catalyzed click chemistry to form novel N-perfluoroalkyl triazoles. Surprisingly, they are more reactive in the click reaction with alkynes than nonfluorinated alkyl azides. The method opens the door to broader use of click chemistry, which has become invaluable to biochemistry and polymer science researchers.
Zsófia E. Blastik, Svatava Voltrová, Václav Matoušek, Bronislav Jurásek, David W. Manley, Blanka Klepetářová, Petr Beier:
Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide–Alkyne Cycloaddition.
Angewandte Chemie International Edition, online from December 5, 2016.
The original ANIE article was also featured in Chemical & Engineering News.