Recent Advances of C—H Phosphonylation of (Hetero)arenes under Electrochemical Conditions

doi:10.6023/cjoc202506033

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (12): 4290-4297.DOI: 10.6023/cjoc202506033 Previous Articles Next Articles

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(杂)芳烃的电化学碳-氢膦酰化反应研究进展

刘若雨^a^,^*(), 梁炳玉^b, 陈书阳^a, 孙红先^a, 孙一冰^a, 叶勇^c^,^*()

^a 南阳师范学院化学与制药工程学院河南南阳 473000
^b 河南省科学院质量检验与分析测试研究中心郑州 450000
^c 郑州大学化学学院郑州 450000

收稿日期:2025-06-26 修回日期:2025-08-08 发布日期:2025-10-09
通讯作者: 刘若雨, 叶勇
基金资助:
南阳师范学院(2025STP013); 南阳科技重大专项(24KJGG015)

Recent Advances of C—H Phosphonylation of (Hetero)arenes under Electrochemical Conditions

Ruoyu Liu^a^,^*(), Bingyu Liang^b, Shuyang Chen^a, Hongxian Sun^a, Yibing Sun^a, Yong Ye^c^,^*()

^a College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473000
^b Quality Inspection and Analysis Testing Research Center, Henan Academy of Sciences, Zhengzhou 450000
^c College of Chemistry, Zhengzhou University, Zhengzhou 450000

Received:2025-06-26 Revised:2025-08-08 Published:2025-10-09
Contact: Ruoyu Liu, Yong Ye
Supported by:
Nanyang Normal University(2025STP013); Nanyang Science and Technology Major Project(24KJGG015)

Phosphonylated (hetero)arenes, as an important class of organophosphorus compounds, exhibit broad application value in fields such as organic catalysis, medicinal chemistry, and materials science. Among various synthetic approaches, the C—H phosphonylation of (hetero)arenes stands out as one of the most efficient strategies for synthesizing these compounds due to its atom economy and step simplicity. In recent years, with the rapid development of organic electrochemistry, significant breakthroughs have been achieved in electrochemically driven C—H phosphonylation. Compared with traditional methods, the electrochemical strategy offers distinct advantages: (1) it replaces chemical oxidants with electrons, improving atom economy, and (2) it demonstrates excellent functional group compatibility under mild conditions. This review summarizes the latest advances in the electrochemical C—H phosphonylation of (hetero)arenes, with a focus on reaction mechanisms and substrate scope. For clarity, the discussed reaction systems are categorized into two major classes based on the electrolysis mode (direct electrolysis vs. indirect electrolysis).

Key words: organic electrosynthesis, electrooxidation, electrocatalysis, phosphonylation, (hetero)arenes

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Ruoyu Liu, Bingyu Liang, Shuyang Chen, Hongxian Sun, Yibing Sun, Yong Ye. Recent Advances of C—H Phosphonylation of (Hetero)arenes under Electrochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4290-4297.

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Fig. & Tab. 10

Scheme 1. Direct electrochemical phosphorylation of quinoxalinones

Scheme 2. Direct electrochemical phosphorylation of N-unpro- tected quinoxalinones

Scheme 3. Electrochemical cross-dehydrogenative coupling of 2-phenylimidazo[1,2-a]pyridines and trialkylphosphites

Scheme 4. Electrochemical C—H phosphorylation of acridine compounds

Scheme 5. Phosphorylation of arenes under electrochemical continuous flow conditions

Scheme 6. Mn-catalyzed electrochemical cross-coupling of heteroarenes with diphenylphosphine oxides

Scheme 7. Electrocatalytic C—H phosphorylation of metallocenes

Scheme 8. Rh(III)-catalyzed electrochemical dehydrogenative coupling of arenes with diphenylphosphine oxides

Scheme 9. Ni-catalyzed electrochemical phosphorylation of (hetero)arenes

Scheme 10. Ru-catalyzed electrochemical ortho/para-selective C—H phosphorylation of arenes

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(杂)芳烃的电化学碳-氢膦酰化反应研究进展

Recent Advances of C—H Phosphonylation of (Hetero)arenes under Electrochemical Conditions

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Fig. & Tab. 10

References 18

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