Synthesis of Functionalized Indoles by an Iridium-Catalyzed N-H Insertion Cascade: Nucleophilic Cyclization of
Xiaogang Wang1, Chi Yang1, Di Chen2
1Shaanxi Key Laboratory of Comprehensive Utilization of Tailings Resources, Shaanxi Engineering Research Center for Mineral Resources Clean and Efficient Conversion and New Materials, College of Chemical Engineering and Modern Materials, Shangluo University, Shangluo 726000, China.
Abstract:
A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly of densely functionalized indoles. This new catalytic process represents the first example of a cascade intramolecular nucleophilic cyclization by the N-H insertion of amines. Various naphthylamines and α-diazocarbonyl compounds could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to novel heterocyclic analogues not easily accessible by other methods.
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