Electrochemical hydrocarboxylation of enol derivatives with CO2: access to β-acetoxycarboxylic acids
Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides beta-acetoxycarboxylic acids in 25-66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols.
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| Published in | Chemical communications (Cambridge, England) Vol. 60; no. 62; pp. 8099 - 8102 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
30.07.2024
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X 1364-548X |
| DOI | 10.1039/d4cc02831g |
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| Abstract | Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides beta-acetoxycarboxylic acids in 25-66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols. |
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| AbstractList | Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides β-acetoxycarboxylic acids in 25–66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols. Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides β-acetoxycarboxylic acids in 25-66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols.Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides β-acetoxycarboxylic acids in 25-66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols. Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides beta-acetoxycarboxylic acids in 25-66% yields, in contrast to the electrolysis of ketones, silyl enol ethers and vinyl tosylates with CO2, which leads mainly to alcohols. |
| Author | Terent'ev, Alexander O. Ilovaisky, Alexey I. Vil', Vera A. Bityukov, Oleg V. He, Liang-Nian Ustyuzhanin, Alexander O. Merkulova, Valentina M. Sokolovskiy, Pavel V. |
| Author_xml | – sequence: 1 givenname: Alexander O. surname: Ustyuzhanin fullname: Ustyuzhanin, Alexander O. organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 2 givenname: Oleg V. surname: Bityukov fullname: Bityukov, Oleg V. organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 3 givenname: Pavel V. orcidid: 0000-0002-8333-1088 surname: Sokolovskiy fullname: Sokolovskiy, Pavel V. organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 4 givenname: Valentina M. surname: Merkulova fullname: Merkulova, Valentina M. organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 5 givenname: Alexey I. surname: Ilovaisky fullname: Ilovaisky, Alexey I. organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 6 givenname: Liang-Nian orcidid: 0000-0002-6067-5937 surname: He fullname: He, Liang-Nian organization: Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China – sequence: 7 givenname: Vera A. orcidid: 0000-0002-6847-6035 surname: Vil' fullname: Vil', Vera A. email: vil@ioc.ac.ru organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia – sequence: 8 givenname: Alexander O. orcidid: 0000-0001-8018-031X surname: Terent'ev fullname: Terent'ev, Alexander O. email: terentev@ioc.ac.ru organization: Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prospekt, Moscow 119991, Russia |
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| Cites_doi | 10.1016/j.electacta.2011.03.061 10.1002/advs.201900137 10.1021/acs.orglett.3c01033 10.1002/cjoc.201700742 10.1002/tcr.202100081 10.1002/celc.201300206 10.1002/anie.202101818 10.1039/d3qo00280b 10.1002/chem.202204073 10.1016/j.jelechem.2011.11.001 10.1002/celc.201900200 10.1016/j.jcou.2024.102753 10.1016/j.jelechem.2007.02.014 10.1021/jacs.9b13305 10.1134/S1070428021080018 10.1002/cjoc.201700740 10.1021/acs.orglett.1c02738 10.1002/adma.201701784 10.1021/jo7025788 10.1002/chem.201901082 10.1039/d2cc05242c 10.1021/acs.joc.1c01224 10.1149/1945-7111/ab72ed 10.1002/aesr.202100001 10.1002/chem.202203228 10.1039/c5cp00095e 10.1016/j.gce.2021.12.001 10.1002/anie.202105490 |
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| Keywords | FACILE SYNTHESIS AROMATIC KETONES REDUCTION OPERATIVE PARAMETERS CARBON-DIOXIDE ELECTROCARBOXYLATION CARBOXYLIC-ACIDS |
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| Snippet | Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides beta-acetoxycarboxylic acids in 25-66% yields, in... Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides β-acetoxycarboxylic acids in 25–66% yields, in... Electrochemical hydrocarboxylation of enol acetates with CO2 is developed. The disclosed process provides β-acetoxycarboxylic acids in 25-66% yields, in... |
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| SubjectTerms | Acetates Alcohols Carbon dioxide Chemistry Chemistry, Multidisciplinary Electrolysis Ethers Ketones Physical Sciences Science & Technology |
| Title | Electrochemical hydrocarboxylation of enol derivatives with CO2: access to β-acetoxycarboxylic acids |
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