Carbonyl-Assisted Iridium-Catalyzed C-H Amination Using 2,2,2-Trichloroethoxycarbonyl Azide.

The carbonyl-directed, mono C-H amination of arenes has been achieved using [Cp*Ir(III)Cl] as the catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating reagent. The amination proceeds smoothly with a variety of arylcarbonyl compounds, including alkyl and vinyl arylketones, secondary and tertiary aryl amides, and acetyl indoles. The resulting -TrocNH arylcarbonyl compounds are easily transformed to the corresponding free arylamines, aryl carbamates, or aryl ureas.