Synthesis of Functionalized\nIndoles by an Iridium-Catalyzed\nN–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines\nwith α‑Diazocarbonyl Compounds

A novel\niridium-catalyzed [3 + 2] annulation of naphthylamines\nand α-diazocarbonyl compounds was developed for the rapid assembly\nof densely functionalized indoles. This new catalytic process represents\nthe first example of a cascade intramolecular nucleophilic cyclization\nby the N–H insertion of amines. Various naphthylamines and\nα-diazocarbonyl compounds could be obtained in high yields with\nexcellent functional group tolerance. The reaction affords valuable\nindole derivatives, enabling expedient access to novel heterocyclic\nanalogues not easily accessible by other methods.