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Electrochemical Decarboxylative Coupling of <i>N</i>‐Substituted Glycines under Air: Access to C3‐Aminomethylated Imidazo[1,2‐<i>a</i>]pyridines

Sifeng Li, Xingchen Li, Xingchen Li, Taimin Wang, Qingjing Yang, Zijun Ouyang, Jieyu Chen, Hongbin Zhai, Xiao Li, Xiao Li, Bin Cheng

2022Advanced Synthesis & Catalysis23 citationsDOI

Abstract

Abstract An electrochemical decarboxylative aminomethylation reaction of imidazo[1,2‐ a ]pyridines with various N ‐substituted glycines in acetonitrile at room temperature has been described. The reaction could be conducted under light‐free, catalyst‐free, oxidant‐free, and air conditions, affording the C3‐aminomethylated imidazo[1,2‐ a ]pyridines in good to high yields. Remarkably, N ‐aryl, N , N ‐dialkyl, and N ‐alkyl‐ N ‐aryl glycines are all well‐tolerated in this easily handled protocol, which further expands the chemical space of bioactive imidazo[1,2‐ a ]pyridine derivatives. magnified image

Topics & Concepts

ChemistryArylAcetonitrileElectrochemistryAlkylDecarboxylationPyridineCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysical chemistryElectrodeRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry