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Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

Qi-Qi Hu, Yanting Gao, Jiachen Sun, Jingjing Gao, Hong-Xiao Mu, Yi‐Ming Li, Yanan Zheng, Kairui Yang, Yanping Zhu

2021Organic Letters29 citationsDOI

Abstract

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2'-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2'-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Topics & Concepts

ChemistryAnnulationCatalysisImineAromatizationIodineLigand (biochemistry)Combinatorial chemistrySubstrate (aquarium)DenticityBifunctionalCopperMedicinal chemistryOrganic chemistryMetalReceptorBiochemistryOceanographyGeologyCatalytic C–H Functionalization MethodsMulticomponent Synthesis of HeterocyclesSynthesis of Indole Derivatives