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Rhodium-Catalyzed Annulation of Tertiary Aniline N‑Oxides to N‑Alkylindoles: Regioselective C–H Activation, Oxygen-Atom Transfer, and N‑Dealkylative Cyclization

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journal contribution
posted on 06.05.2016, 00:00 by Bin Li, Hong Xu, Huanan Wang, Baiquan Wang
[Cp*RhIII]-catalyzed annulation of tertiary aniline N-oxides with alkynes was reported to achieve the challenging ortho C–H functionalization of tertiary anilines via N–O bond acting as a traceless directing group. More significantly, this system represents the first example which integrates C–H activation, oxygen-atom transfer, and N-dealkylative cyclization in one reaction. This unprecedented coupling reaction has allowed the construction of N-alkylindole derivatives in high efficiency with broad substrate scope and good functional group tolerance.