Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C–H Activation/Annulation of Arylhydrazines with Iodonium Ylides
He Li, Haichun Gu, Ye Lu, Ning Xu, Narenchaoketu Han, Jiaqi Li, Jinghai Liu, Jing-Lin Liu
Abstract
The rhodium(III)-catalyzed C-H activation followed by intramolecular annulation reactions between arylhydrazines and iodonium ylides under suitable conditions has been described. Tetrahydrocarbazol-4-ones are readily achieved with moderate to excellent yields. The synthetic protocol features a wide range of substrates with high functional group tolerance. The gram-scale reaction and derivatization of the product demonstrate the synthetic practicality and utilization of this method.
Topics & Concepts
AnnulationChemistryRhodiumIntramolecular forceCatalysisDerivatizationCombinatorial chemistryReaction conditionsFunctional groupMedicinal chemistryOrganic chemistryHigh-performance liquid chromatographyPolymerCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions