Rh(III)‐Catalyzed C(sp <sup>2</sup> )–H and C(sp <sup>2</sup> )–C(sp <sup>2</sup> ) Bond Activation of Aryl Oximes with CF <sub>3</sub> ‐Imidoyl Sulfoxonium Ylides: Access to <i>N</i> ‐(2‐Cyanoaryl)‐3‐(Trifluoromethyl)isoquinolin‐1( <i>2H</i> )‐Imines
Pinyi Li, Jian Chen, Zuguang Yang, Zhengkai Chen
Abstract
Abstract A rhodium(III)‐catalyzed redox‐neutral C−H and C−C bond activation reaction of aryl oximes and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been described, producing a wide variety of N ‐(2‐cyanoaryl)‐3‐(trifluoromethyl)isoquinolin‐1( 2H )‐imines in moderate to excellent yields. The transformation might involve a consecutive C(sp 2 )–H bond activation, intramolecular spiro‐cyclization, C−C bond activation and N−O bond cleavage sequence. This developed protocol provides a direct entry to diverse trifluoromethyl and nitrile‐containing heterocycles with the generation of water and dimethyl sulfoxide as by‐products.
Topics & Concepts
ChemistryTrifluoromethylArylIntramolecular forceBond cleavageMedicinal chemistryCatalysisRhodiumNitrileSulfoxideStereochemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsFluorine in Organic Chemistry