Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3<i>H</i>‐indoles and CF<sub>3</sub>‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11<i>H</i>‐Isoindolo[2,1‐a]indoles
Zuguang Yang, Pinyi Li, Zhengkai Chen, Xiao‐Feng Wu
Abstract
Abstract A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3 H ‐indoles and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety of trifluoroacetimidoyl‐substituted 11 H ‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves C−H imidoylmethylation, tautomerization and AgOAc‐mediated C−N bond formation sequence. The reaction could be scaled up to 2 mmol scale.
Topics & Concepts
ChemistryAnnulationTautomerCatalysisArylRhodiumCascadeMedicinal chemistryCascade reactionStereochemistryCombinatorial chemistryOrganic chemistryAlkylChromatographyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions