Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination

0580550 - ÚOCHB 2025 RIV DE eng J - Článek v odborném periodiku
Baris, Norbert - Dračínský, Martin - Tarábek, Ján - Filgas, J. - Slavíček, P. - Ludvíková, Lucie - Boháčová, Soňa - Slanina, Tomáš - Klepetářová, Blanka - Beier, Petr
Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination.
Angewandte Chemie - International Edition. Roč. 63, č. 2 (2024), č. článku e202315162. ISSN 1433-7851. E-ISSN 1521-3773
Grant CEP: GA ČR(CZ) GA23-04659S; GA MŠMT(CZ) LTC20076
Institucionální podpora: RVO:61388963
Klíčová slova: azides * aziridines * nNitrene * photocatalysis * visible light
Obor OECD: Organic chemistry
Impakt faktor: 16.6, rok: 2022
Způsob publikování: Open access
https://doi.org/10.1002/anie.202315162

N-Trifluoromethylated organics may be applied in drug design, agrochemical synthesis, and materials science, among other areas. Yet, despite recent advances in the synthesis of aliphatic, cyclic and heterocyclic N-trifluoromethyl compounds, no strategy based on trifluoromethyl nitrene has hitherto been explored. Here we describe the formation of triplet trifluoromethyl nitrene from azidotrifluoromethane, a stable and safe-to-use precursor, by visible light photocatalysis. The addition of CF3N to alkenes via biradical intermediates afforded previously unknown aziridines substituted with trifluoromethyl group on the nitrogen atom. The obtained aziridines were converted into either N-trifluoromethylimidazolines, via formal [3+2] cycloaddition with nitriles, mediated by a Lewis acid, or into N-trifluoromethylaldimines, via ring opening and aryl group migration mediated by a strong Bronsted acid. Our findings open new opportunities for the development of novel classes of N-CF3 compounds with possible applications in the life sciences.
Trvalý link: https://hdl.handle.net/11104/0349311