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
Affiliations
Rong Sun
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
Fan Hu
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
Haoyang Jiang
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
Wenbin Du
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
Chaochao Zhang
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
Tianhao Chang
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
Yuling Zhou
State Key Laboratory of Biocatalysis and Enzyme Engineering, School of Life Sciences, Hubei University, Wuhan 430062, P.R. China
Pan Wu
State Key Laboratory of Biocatalysis and Enzyme Engineering, School of Life Sciences, Hubei University, Wuhan 430062, P.R. China; Corresponding author
Dingyu Li
Department of Oncology, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, 1095 Jiefang Avenue, Qiaokou District, Wuhan, P.R. China; Corresponding author
Yue Weng
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; Corresponding author
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.
