CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization to access 5,6-dihydro-pyrrolo[2,1-<i>a</i>]isoquinolines
Zhiyu Xie, Fei Li, Liang‐Feng Niu, Hongbing Li, Jincai Zheng, Ruijing Han, Zhiyu Ju, Shanshan Li, Dandan Li
Abstract
An efficient and enviromentally friendly CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization cascade was realized with N-substituted tetrahydroisoquinolines and electron-deficient olefins. Under the mild conditions, the reaction proceeded smoothly and displayed excellent functional group tolerance, affording 5,6-dihydro-pyrrolo[2,1-a]isoquinolines in good to high yields. This protocol exhibits a broad substrate scope to both N-alkyl tetrahydroisoquinolines and dipolarophile substrates.
Topics & Concepts
AromatizationChemistryCycloadditionOxidative phosphorylationCatalysisSubstrate (aquarium)Functional groupAlkylMedicinal chemistryCombinatorial chemistryOrganic chemistryBiochemistryGeologyOceanographyPolymerCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesCyclopropane Reaction Mechanisms