One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N‑Alkylanilines and Rh(III)-Catalyzed C–H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C–H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.