Over the past decades, new transition metal systems for the direct C-H functionalizations of arenes have been extensively explored and rapidly evolved up to date, which enable the regioselective installation of various functional groups into the desired C-H bonds of the substrates. The transformation of arenes to anilines through the catalytic C-H amidation (C-N bond-forming reaction) has been a steady issue in chemical synthesis due to the importance of anilines as key building units in medicinal and material chemistry. Recently, our group has successfully demonstrated that cationic Cp*Rh and Ir complexes initiate the direct C-H amidation of 2-phenylpyridine with azides as the amino source, in which the iridium catalysis features mild C-H bond activation, high functional group tolerance, and strong preference for relatively stable azides such as acyl azide and tosyl azide. Herein we present new substrate scope and control of stereoselectivity in the Ir(III)-catalyzed C-H amidation with organic azides. Additionally, we describe details of the rational design of the catalytic system for the asymmetric C-H amidation.

Cationic Cp*Ir(?)-catalyzed direct C-H amidation of arenes using azides as the nitrogen source

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.