Mészáros Ádám, Székely Anna, Stirling András, Novák Zoltán
ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, 1117, Budapest, Hungary.
Current address: Max Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 2, 45470, Mülheim an der Ruhr, Germany.
Angew Chem Int Ed Engl. 2018 May 28;57(22):6643-6647. doi: 10.1002/anie.201802347. Epub 2018 Apr 30.
The synthesis of fluorinated compounds and their use as pharmaceutical ingredients or synthetic building blocks have been in the focus of chemical and medicinal research. However, the efficient synthesis of trifluoromethylated nitrogen heterocycles is sometimes challenging. Herein, we disclose a simple aziridination process that relies on the use of amines and novel alkenyl iodonium reagents for the synthesis of strained, trifluoromethylated heterocycles. With the utilization of a newly designed and bench-stable but highly reactive hypervalent alkenyl iodonium species, these three-membered-ring heterocyclic compounds can be efficiently constructed from simple amines under mild conditions in the absence of transition-metal catalysts. The special reactivity of the new trifluoropropenyl synthon towards nucleophilic centers could be exploited in more general cyclization and alkenylation reactions in the future.
含氟化合物的合成及其作为药物成分或合成砌块的应用一直是化学和药物研究的重点。然而，三氟甲基化氮杂环的高效合成有时具有挑战性。在此，我们公开了一种简单的氮杂环丙烷化过程，该过程依赖于使用胺类和新型烯基碘鎓试剂来合成具有张力的三氟甲基化杂环。通过使用新设计的、易于保存且反应活性高的高价烯基碘鎓物种，这些三元环杂环化合物可以在无过渡金属催化剂的温和条件下由简单的胺类高效构建。未来，新型三氟丙烯基合成子对亲核中心的特殊反应活性可应用于更广泛的环化和烯基化反应中。
