Iridium-Catalyzed Direct C-H Amination with Alkylamines: Facile Oxidative Insertion of Amino Group into Iridacycle

Abstract

Described herein is the development of Cp∗Ir(III)-catalyzed direct arene C-H amination using alkylamines as an amino source. This C-N bond formation showcases a notable example of cross-dehydrogenative coupling to install an amino functionality at the ortho-position of benzamide substrates. Mechanistic studies including the isolation of an amine-bound iridacyclic intermediate along with a set of chemical oxidations demonstrated the Ir-catalyzed inner-sphere C-H amination with primary alkylamines for the first time. © 2015 American Chemical Society