Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β‑Diketones and β‑Ketoesters with Carboxylic Acids
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%,...
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| Published in | Journal of organic chemistry Vol. 84; no. 3; pp. 1448 - 1460 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.02.2019
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. The electrochemically induced cross-dehydrogenative C-O coupling of beta-diketones and beta-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. 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.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. |
| Author | Kokorekin, Vladimir A Terent’ev, Alexander O Matveeva, Olesya K Nikishin, Gennady I Vil’, Vera A Bityukov, Oleg V |
| AuthorAffiliation | D. I. Mendeleev University of Chemical Technology of Russia N. D. Zelinsky Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: N. D. Zelinsky Institute of Organic Chemistry – name: D. I. Mendeleev University of Chemical Technology of Russia |
| Author_xml | – sequence: 1 givenname: Oleg V surname: Bityukov fullname: Bityukov, Oleg V organization: N. D. Zelinsky Institute of Organic Chemistry – sequence: 2 givenname: Olesya K surname: Matveeva fullname: Matveeva, Olesya K organization: D. I. Mendeleev University of Chemical Technology of Russia – sequence: 3 givenname: Vera A surname: Vil’ fullname: Vil’, Vera A organization: N. D. Zelinsky Institute of Organic Chemistry – sequence: 4 givenname: Vladimir A surname: Kokorekin fullname: Kokorekin, Vladimir A organization: N. D. Zelinsky Institute of Organic Chemistry – sequence: 5 givenname: Gennady I surname: Nikishin fullname: Nikishin, Gennady I organization: N. D. Zelinsky Institute of Organic Chemistry – sequence: 6 givenname: Alexander O orcidid: 0000-0001-8018-031X surname: Terent’ev fullname: Terent’ev, Alexander O email: alterex@yandex.ru organization: D. I. Mendeleev University of Chemical Technology of Russia |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30618255$$D View this record in MEDLINE/PubMed |
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| SubjectTerms | carbon carboxylic acids chemical reactions chemical structure Chemistry Chemistry, Organic dimethyl sulfoxide electric current electrochemistry electrodes organic chemistry oxidants Physical Sciences platinum Science & Technology solvents |
| Title | Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β‑Diketones and β‑Ketoesters with Carboxylic Acids |
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