Carboxylate-Assisted Iridium (III)-Catalyzed C(sp2)-H Amidation of 2-Aroylimidazoles With Dioxazolones.

Abstract

The Ir(III)-catalyzed ortho C-H amidation of 2-aroylimidazoles with 3-aryldioxazolones as an amidating reagent is reported. The method provides a broad substrate scope with wide functional group compatibility. Mechanistic studies indicate that C-H bond cleavage is reversible and appears not to be the rate-determining step. The presence of an electron-donating group in the 2-aroylimidazoles and an electron-withdrawing group in the 3-aryldioxazoles significantly accelerates the reaction, suggesting that nitrene insertion is the rate-determining step.