Photocatalytic generation of trifluoromethyl nitrene for alkene aziridination
Scientists led by Petr Beier from IOCB Prague in collaboration with colleagues from UCT Prague have for the first time generated triplet trifluoromethyl nitrene under mild photocatalytic conditions. The iridium photocatalyst (fac-Ir(ppy)3) excited by blue light is capable of triplet energy transfer to the thermally stable azidotrifluoromethane CF3N3 which loses dinitrogen and generates triplet trifluoromethyl nitrene.
This new reactive intermediate easily undergoes an addition reaction to diverse alkenes via biradical intermediates, and thus afforded previously unknown aziridines bearing the trifluoromethyl group on the nitrogen atom. The aziridines were converted into novel class of N-CF3 compounds N-trifluoromethylimidazolines and N-trifluoromethylaldimines, which can be further used in drug design, agrochemical synthesis, or material sciences.
These results were published in Angewandte Chemie with Norbert Baris as the first author.
Read the paper: Baris, N.; Dračínský, M.; Tarábek, J.; Filgas, J.; Slavíček, P.; Ludvíková, L.; Boháčová, S.; Slanina, T.; Klepetářová, B.; Beier, P. Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination. Angew. Chem. Int. Ed. 2023, e202315162. https://doi.org/10.1002/anie.202315162