Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides

A disclosed technique employs electrochemical dehydrogenative cross-coupling to create organophosphates, utilizing phosphites compounds with arenols. Inorganic iodide salts serve dual roles as redox catalysts and electrolytes in an undivided cell, omitting the need for external oxidants or bases. Initial mechanistic investigations indicate the reaction unfolds via an electro-oxidative radical pathway, facilitating the formation of P-O bonds, leading to the generation of oxygen radicals in the formation of acetylaminophenol. This environmentally friendly approach offers excellent tolerance to various functional groups, achieves high yields (up to 95% isolated yield), and accommodates a wide range of substrates, showcasing its utility for practical synthesis applications.

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Publication Details

Journal
iScience
Published
2024-08-05
DOI
https://doi.org/10.1016/j.isci.2024.110487
Citations
5
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.25

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article

Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides

Pan Wu, Rong Sun, Wenbin Du, Tianhao Chang et al.
5 citations
iScience
Radical Photochemical Reactions
1.25
article

Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides

Pan Wu, Rong Sun, Wenbin Du, Tianhao Chang, Haoyang Jiang, Yue Weng, Yuling Zhou, Chaochao Zhang, Fan Hu, Dingyu Li
article en
5 citations

Abstract

A disclosed technique employs electrochemical dehydrogenative cross-coupling to create organophosphates, utilizing phosphites compounds with arenols. Inorganic iodide salts serve dual roles as redox catalysts and electrolytes in an undivided cell, omitting the need for external oxidants or bases. Initial mechanistic investigations indicate the reaction unfolds via an electro-oxidative radical pathway, facilitating the formation of P-O bonds, leading to the generation of oxygen radicals in the formation of acetylaminophenol. This environmentally friendly approach offers excellent tolerance to various functional groups, achieves high yields (up to 95% isolated yield), and accommodates a wide range of substrates, showcasing its utility for practical synthesis applications.

iScienceVol. 27(9)
Tongji Hospital (CN), Huazhong University of Science and Technology (CN), Hubei University (CN)
National Natural Science Foundation of China, National Aerospace Science Foundation of China, State Key Laboratory of Water Resources and Hydropower Engineering Science, Engineering and Technology Research Center of Liupanshan Resources
Clean water and sanitation
Openalex Percentile: Top 23%
Radical Photochemical Reactions
1.25
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Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides — Pan Wu, Rong Sun, et al. · iScience (2024) | TGRS Research Map | TGRS