Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Bityukov O. V., Matveeva O. K., Vil V. A., Kokorekin V. A., Nikishin G. I., Terent'Ev A. O.
Journal of Organic Chemistry
Vol.84, Issue3, P. 1448-1460
Опубликовано: 2019
Тип ресурса: Статья
DOI:10.1021/acs.joc.8b02791
Аннотация:
The electrochemically induced cross-dehydrogenative C-O coupling of β-diketones and β-ketoesters (C-H reagents) with carboxylic acids (O-H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C-O coupling products in high yields, up to 92[%], using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant. Copyright © 2019 American Chemical Society.
Ключевые слова:
Electrodes; Ketones; C-o couplings; High current densities; Important features; Keto ester; Platinum electrodes; Selective formation; Stoichiometric oxidant; Undivided cell; Carboxylic acids; acetic acid; beta ketoester derivative; bromine; carbon; carboxylic acid; diketone; dimethyl sulfoxide; ester derivative; graphite; hydrogen; platinum; unclassified drug; Article; chemical structure; controlled study; current density; electric current; electrochemistry; oxidative coupling; reaction analysis; stoichiometry; synthesis
Язык текста: Английский
ISSN: 1520-6904
Bityukov O. V.
Matveeva O. K.
Vil V. A.
Kokorekin V. A. Vladimir Alekseevich 1987-
Nikishin G. I.
Terent'Ev A. O.
Битюков О. В.
Матвеева О. К.
Вил В. А.
Кокорекин В. А. Владимир Алексеевич 1987-
Никишин Г. И.
Терент'Ев А. О.
Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Текст визуальный непосредственный
Journal of Organic Chemistry
American Chemical Society
Vol.84, Issue3 P. 1448-1460
2019
Статья
Electrodes Ketones C-o couplings High current densities Important features Keto ester Platinum electrodes Selective formation Stoichiometric oxidant Undivided cell Carboxylic acids acetic acid beta ketoester derivative bromine carbon carboxylic acid diketone dimethyl sulfoxide ester derivative graphite hydrogen platinum unclassified drug Article chemical structure controlled study current density electric current electrochemistry oxidative coupling reaction analysis stoichiometry synthesis
The electrochemically induced cross-dehydrogenative C-O coupling of β-diketones and β-ketoesters (C-H reagents) with carboxylic acids (O-H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C-O coupling products in high yields, up to 92[%], using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant. Copyright © 2019 American Chemical Society.