Iron porphyrin-catalysed C(sp3)–H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds

Abstract

Transition metal-catalysed direct C–N bond formation via nitrenoid (metal–imido/nitrene complexes) insertion, such as C–H bond amination, is a powerful strategy for preparing nitrogen-containing organic compounds. In this context, metal catalysts based on iron are appealing due to iron's high Earth abundance and biocompatibility. Herein, we demonstrate that iron(III) NHC porphyrin-catalysed C(sp³)–H amination with alkyl azides, using [Fe^III(TDCPP)(IMe)₂]I (H₂TDCPP = tetrakis(2,6-dichlorophenyl)porphyrin, IMe = 1,3-dimethylimidazol-2-ylidene) as a catalyst, offers a complementary approach for the synthesis of structurally complex organic compounds as exemplified by the synthesis of a panel of nitrogen-containing skeletons that are representative examples of various families of natural products and bioactive compounds.