Synthesis of 2-Trifluoromethylindolines via Rh(III)-Catalyzed Chelation-Assisted C–H Bond Activation and Annulation of Anilines with CF₃-Imidoyl Sulfoxonium Ylides

Rh(III)-catalyzed C-H bond activation and annulation of <i>N</i>-pyrimidyl-substituted anilines with CF₃-imidoyl sulfoxonium ylides (TFISYs) have been disclosed, affording a variety of 2-trifluoromethylindolines that contain a quaternary carbon center. A cascade C-H imidoylmethylation, tautomerization, and intramolecular nucleophilic addition sequence is involved in the transformation. The reaction could be scaled up to 2 mmol. The protocol provides facile and straightforward access to biologically important indoline scaffolds with a trifluoromethyl and an amino functionality.