Rh(III)-Catalyzed C–H Annulation of <i>N</i>-Nitrosoanilines with Iodonium Ylides for the Synthesis of <i>N</i>-Alkyl Indoles
Chaoshui Liu, Qiuzi Dai, Yaqian Li, Chuhan Huang, Lijuan Guo, Zi Yang
Abstract
A novel protocol for synthesizing N -alkyl indoles from readily available N -nitrosoanilines and iodonium ylides through the rhodium(III)-catalyzed C–H bond activation/intramolecular cyclization reaction has been described. This strategy employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate yields under mild reaction conditions, providing a straightforward approach to access structurally diverse and valuable N -alkyl indole derivatives.
Topics & Concepts
AnnulationAlkylChemistryReactivity (psychology)Indole testRhodiumCatalysisIntramolecular forceMedicinal chemistryNitrosoStereochemistryCombinatorial chemistryOrganic chemistryAlternative medicinePathologyMedicineCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions