Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination
Norbert Baris, Martin Dračínský, Ján Tarábek, Josef Filgas, Petr Slavı́ček, Lucie Ludvíková, Soňa Boháčová, Tomáš Slanina, Blanka Klepetářová, Petr Beier
Abstract
Abstract 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 CF 3 N 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 Brønsted acid. Our findings open new opportunities for the development of novel classes of N ‐CF 3 compounds with possible applications in the life sciences.