American Chemical Society
jo0c02776_si_001.pdf (10.92 MB)

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

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journal contribution
posted on 2020-12-23, 13:34 authored by Tengda Si, Hun Young Kim, Kyungsoo Oh
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.