Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines
Quan‐Xing Zi, Minyan Li, Jielun Cong, Guogang Deng, Shengzu Duan, Meng Jia Yin, Wen Chen, Jing Hong, Xiaodong Yang, Patrick J. Walsh
Abstract
Herein is introduced the application of "super-electron-donor"(SED) 2-azaallyl anions in a tandem reduction/radical cyclization/radical coupling/aromatization protocol that enables the rapid construction of isoquinolines. The value of this transition-metal-free method is highlighted by the wide range of isoquinoline ethyl amines prepared with good functional group tolerance and yields. An operationally simple gram scale synthesis is also conducted, confirming the scalability.
Topics & Concepts
ChemistryIsoquinolineAromatizationTandemFunctional groupCombinatorial chemistryRadical ionMedicinal chemistryOrganic chemistryCatalysisIonComposite materialMaterials sciencePolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques