iScience (Sep 2024)

Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides

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

Journal volume & issue
Vol. 27, no. 9
p. 110487

Abstract

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Summary: 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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