Rhodium-Catalyzed Transarylation of Benzamides: C–C Bond vs C–N Bond Activation
Yang Long, Zhishan Su, Y.-Q. Zheng, Shiyu He, Jing Zhong, Haifeng Xiang, Xiangge Zhou
Abstract
A rhodium-catalyzed transarylation of benzamides via selective C–C bond activation with arylboronic acids was described, which was distinct from the conventional metal-catalyzed C–N bond activation. This transformation exhibited good functional group compatibility with yields up to 88%, offering a practical approach for the construction and functionalization of benzamides. Preliminary experimental and computational studies revealed the selectivity of metal insertion into the C–C bond or the C–N bond was greatly affected by substituents on the amide’s N atom.
Topics & Concepts
RhodiumChemistryCatalysisAmideSurface modificationMetalMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryPhysical chemistryChemical Synthesis and AnalysisCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic Chemistry