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

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.

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Publication Details

Journal
Organic Letters
Published
2024-10-25
DOI
https://doi.org/10.1021/acs.orglett.4c03574
Citations
10
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.50

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article

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

Li‐Rong Wen, Lin‐Bao Zhang, Weisi Guo, Ming‐Zhong Guo et al.
10 citations
Organic Letters
Radical Photochemical Reactions
2.50
article

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

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

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.

Organic LettersVol. 26(44)
Qingdao University of Science and Technology (CN), Shantou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Shandong Province
Clean water and sanitation
Openalex Percentile: Top 11%
Radical Photochemical Reactions
2.50
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