Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides.

iScience

Hubei Key Laboratory of Precision Manufacturing for Small-molecular Active Pharmaceutical Ingredients, School of Chemistry and Chemical Engineering, State Key Laboratory of Biocatalysis and Enzyme Engineering, Hubei University, Wuhan, P.R. China.

Published: September 2024

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11418147PMC
http://dx.doi.org/10.1016/j.isci.2024.110487DOI Listing

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Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides.

iScience

September 2024

Hubei Key Laboratory of Precision Manufacturing for Small-molecular Active Pharmaceutical Ingredients, School of Chemistry and Chemical Engineering, State Key Laboratory of Biocatalysis and Enzyme Engineering, Hubei University, Wuhan, P.R. China.

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.

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