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Electroreductive C3 Pyridylation of Quinoxalin-2(1<i>H</i>)-ones: An Effective Way to Access Bidentate Nitrogen Ligands

Jiangwei Wen, Xiaoting Yang, Kelu Yan, Hongyun Qin, Jing Ma, Xuejun Sun, Jianjing Yang, Hua Wang

2021Organic Letters48 citationsDOI

Abstract

The construction of functional N-containing active biomolecules and bidentate nitrogen ligands by electroreductive pyridylation of N-heteroaromatics is an eye-catching task and challenge. A simple and practical electroreductive-induced C3 pyridylation of quinoxalin-2(1H)-ones with readily available cyanopyridines is reported. More than 36 examples are supplied, and the reaction performed in >95% yield. The present protocol provides a convenient, efficient, and gram-scale synthesis strategy for a series of new types of potential bidentate nitrogen ligands.

Topics & Concepts

ChemistryDenticityYield (engineering)NitrogenCombinatorial chemistryOrganic chemistryMetalMetallurgyMaterials scienceSynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsRadical Photochemical Reactions