Rhodium-Catalyzed Atroposelective Oxidative C–H/C–H Cross-Coupling Reaction of 1-Aryl Isoquinoline Derivatives with Electron-Rich Heteroarenes
Qiang Wang, Wenwen Zhang, Hao Song, Jian Wang, Chao Zheng, Qing Gu, Shu‐Li You
Abstract
Rhodium(III)-catalyzed enantioselective oxidative C-H/C-H cross-coupling reaction between two arenes is disclosed. With the combination of a chiral CpRh(III) complex and a chiral carboxylic acid additive, the direct coupling reactions between 1-aryl isoquinoline derivatives and electron-rich heteroarenes such as thiophenes, furans, benzothiophenes, and benzofurans are realized via a double C-H functionalization process. A series of axially chiral compounds are obtained in excellent yields and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggest that both C-H bond cleavages may not be the turnover-limiting step.
Topics & Concepts
ChemistryIsoquinolineRhodiumArylEnantioselective synthesisCatalysisOxidative coupling of methaneYield (engineering)Medicinal chemistryOrganic chemistryCombinatorial chemistryAlkylMetallurgyMaterials scienceAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology