Rh(III)-Catalyzed Atroposelective C–H Iodination of 1-Aryl Isoquinolines
Dong‐Song Zheng, Wenwen Zhang, Qing Gu, Shu‐Li You
Abstract
The rhodium-catalyzed enantioselective C–H iodination of 1-aryl isoquinolines under mild conditions is disclosed. Direct C–H iodination of 1-aryl isoquinolines with N -iodosuccinimide (NIS) catalyzed by chiral CpRh(III) complexes afforded a series of axially chiral biaryl iodides in excellent yields and enantioselectivity (up to 99% yield and 97% ee). Furthermore, the atroposelective C–H bromination and chlorination reactions were also compatible. Notably, the axially chiral biaryl iodides could be easily transformed to QUINAP-type and N, N -type chiral ligands.
Topics & Concepts
HalogenationChemistryArylCatalysisEnantioselective synthesisYield (engineering)RhodiumMedicinal chemistryOrganic chemistryCombinatorial chemistryAlkylMaterials scienceMetallurgyAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyCatalytic C–H Functionalization Methods