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Synthesis of Indole-Fused Six-, Seven-, or Eight-Membered N,O-Heterocycles via Rhodium-Catalyzed <i>NH</i>-Indole-Directed C–H Acetoxylation/Hydrolysis/Annulation

Guoshuai Pan, Leipeng Lu, Weihui Zhuang, Qiufeng Huang

2021The Journal of Organic Chemistry13 citationsDOI

Abstract

We report herein the facile synthesis of indole-fused six-, seven-, or eight-membered N,O-heterocycles through rhodium-catalyzed C–H acetoxylation/hydrolysis/annulation. The notable features of this method include C–H acetoxylation using NH-indole as the intrinsic directing group, high functional group compatibility, and construction of indole-fused medium-sized rings.

Topics & Concepts

Indole testAnnulationChemistryRhodiumHydrolysisCatalysisStereochemistryOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis
Synthesis of Indole-Fused Six-, Seven-, or Eight-Membered N,O-Heterocycles via Rhodium-Catalyzed <i>NH</i>-Indole-Directed C–H Acetoxylation/Hydrolysis/Annulation | Litcius