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Mn-Catalyzed Electrochemical Radical Cascade Cyclization toward the Synthesis of Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-one Derivatives

Yong Yuan, Yongfu Zheng, Bizhen Xu, Jia‐Peng Liao, Faxiang Bu, Shengchun Wang, Jianguo Hu, Aiwen Lei

2020ACS Catalysis165 citationsDOI

Abstract

Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we develop a Mn-catalyzed electrochemical radical cascade cyclization reaction that uses electricity as the primary energy input to promote the reaction, leading to a series of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives under exogenous-oxidant-free conditions. It is worth noting that this electrochemical method can not only realize the synthesis of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives but also provides a new strategy for generating alkyl radicals from alkylboronic acids.

Topics & Concepts

ChemistryCatalysisElectrochemistryRadicalCombinatorial chemistryCascadeAlkylRadical cyclizationMedicinal chemistryOrganic chemistryElectrodeChromatographyPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques