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Electrochemically Driven α,β-Dehydrogenation of Flavanones, Azaflavanones, and Thioflavanones

Mei‐Jin Mou, Ming‐Zhong Guo, Quanxin Li, Shao‐Fei Ni, Jian Lv, Weisi Guo, Li‐Rong Wen, Lin‐Bao Zhang

2024Organic Letters14 citationsDOI

Abstract

α,β-Dehydrogenation of flavanones represents an ideal strategy to synthesize various flavones but remains challenging because of the requirements for rigorous conditions. Herein, a straightforward and efficient route for the synthesis of flavones via electrocatalysis is disclosed. This electro-oxidative approach shows a broad substrate scope, including azaflavanones and thioflavanones, which could be performed in an undivided cell without the removal of air or water and in the absence of metal catalysts, ligands, or external oxidants. Moreover, the combination of cyclic voltammetry, square wave voltammetry experiments, and density functional theory (DFT) calculations revealed the plausible mechanism.

Topics & Concepts

ChemistryDehydrogenationCombinatorial chemistryNanotechnologyComputational chemistryOrganic chemistryCatalysisMaterials scienceRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsSynthesis of Organic Compounds
Electrochemically Driven α,β-Dehydrogenation of Flavanones, Azaflavanones, and Thioflavanones | Litcius