Intramolecular, Site-Selective, Iodine-Mediated, Amination of Unactivated (sp3)C–H Bonds for the Synthesis of Indoline Derivatives

The Iodine-mediated oxidative intramolecular amination of anilines via cleavage of unactivated (sp3)­C–H and N–H bonds for the production of indolines is described. This transition-metal-free approach provides a straightforward strategy for producing (sp3)­C–N bonds for use in the preferential functionalization of unactivated (sp3)­C–H bonds over (sp2)­C–H bonds. The reaction could be performed on a gram scale for the synthesis of functionalized indolines.