Journal of the American Chemical Society, volume 122, issue 51, pages 12663-12674
Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones
Mamoru Tobisu
1
,
Naoto Chatani
1
,
Taku Asaumi
1
,
Katsuya AMAKO
1
,
Yutaka Ie
1
,
Yoshiya Fukumoto
1
,
Shinji MURAI
1
Publication type: Journal Article
Publication date: 2000-12-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The ruthenium-catalyzed intermolecular cyclocoupling of ketones (or aldehydes), alkenes (or alkynes), and CO, which leads to γ-butyrolactones, is described. The reaction represents the first example of the catalytic synthesis of heterocycles via an intermolecular carbonylative [2 + 2 + 1] cycloaddition. A wide variety of ketones, such as α-dicarbonyl compounds and N-heterocyclic ketones, can be used in this cycloaddition. The addition of phosphines is quite effective in reactions of α-dicarbonyl compounds. Of the phosphines examined, P(4-CF3C6H4)3 represents the additive of choice. Cyclic olefins, unpolarized terminal olefins, and internal alkynes can be successfully used in the synthesis of highly functionalized lactones. The introduction of a CF3 group to the aromatic portion of an aromatic keto ester accelerates the reaction of the keto ester with ethylene, while the introduction of a MeO group enhances the rate of the reaction of N-heterocyclic ketones with ethylene. The rate of the reaction increases...
Top-30
Citations by journals
2
4
6
8
10
12
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Journal of the American Chemical Society
12 publications, 14.63%
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Angewandte Chemie - International Edition
9 publications, 10.98%
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Angewandte Chemie
9 publications, 10.98%
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Journal of Organic Chemistry
5 publications, 6.1%
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Tetrahedron
5 publications, 6.1%
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Chemical Reviews
5 publications, 6.1%
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Coordination Chemistry Reviews
3 publications, 3.66%
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Organic Letters
3 publications, 3.66%
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Synlett
3 publications, 3.66%
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Chemistry - An Asian Journal
2 publications, 2.44%
|
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Chemical Communications
2 publications, 2.44%
|
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Chinese Journal of Organic Chemistry
1 publication, 1.22%
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Topics in Current Chemistry
1 publication, 1.22%
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Inorganic Chemistry Communication
1 publication, 1.22%
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Journal of Molecular Structure THEOCHEM
1 publication, 1.22%
|
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Tetrahedron Letters
1 publication, 1.22%
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ChemInform
1 publication, 1.22%
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ChemistrySelect
1 publication, 1.22%
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Applied Organometallic Chemistry
1 publication, 1.22%
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ChemCatChem
1 publication, 1.22%
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Chemistry - A European Journal
1 publication, 1.22%
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Inorganic Chemistry
1 publication, 1.22%
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Chemical Science
1 publication, 1.22%
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Synthetic Communications
1 publication, 1.22%
|
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Heterocycles
1 publication, 1.22%
|
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Synthesis
1 publication, 1.22%
|
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Chinese Chemical Letters
1 publication, 1.22%
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Russian Chemical Reviews
1 publication, 1.22%
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2
4
6
8
10
12
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Citations by publishers
5
10
15
20
25
30
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Wiley
29 publications, 35.37%
|
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American Chemical Society (ACS)
26 publications, 31.71%
|
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Elsevier
13 publications, 15.85%
|
|
Thieme
4 publications, 4.88%
|
|
Royal Society of Chemistry (RSC)
3 publications, 3.66%
|
|
Shanghai Institute of Organic Chemistry
1 publication, 1.22%
|
|
Springer Nature
1 publication, 1.22%
|
|
Taylor & Francis
1 publication, 1.22%
|
|
The Japan Institute of Heterocyclic Chemistry
1 publication, 1.22%
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 1.22%
|
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5
10
15
20
25
30
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Tobisu M. et al. Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones // Journal of the American Chemical Society. 2000. Vol. 122. No. 51. pp. 12663-12674.
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Tobisu M., Chatani N., Asaumi T., AMAKO K., Ie Y., Fukumoto Y., MURAI S. Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones // Journal of the American Chemical Society. 2000. Vol. 122. No. 51. pp. 12663-12674.
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TY - JOUR
DO - 10.1021/ja003018i
UR - https://doi.org/10.1021/ja003018i
TI - Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones
T2 - Journal of the American Chemical Society
AU - Asaumi, Taku
AU - AMAKO, Katsuya
AU - Fukumoto, Yoshiya
AU - MURAI, Shinji
AU - Tobisu, Mamoru
AU - Chatani, Naoto
AU - Ie, Yutaka
PY - 2000
DA - 2000/12/01 00:00:00
PB - American Chemical Society (ACS)
SP - 12663-12674
IS - 51
VL - 122
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2000_Tobisu,
author = {Taku Asaumi and Katsuya AMAKO and Yoshiya Fukumoto and Shinji MURAI and Mamoru Tobisu and Naoto Chatani and Yutaka Ie},
title = {Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones},
journal = {Journal of the American Chemical Society},
year = {2000},
volume = {122},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ja003018i},
number = {51},
pages = {12663--12674},
doi = {10.1021/ja003018i}
}
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MLA
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Tobisu, Mamoru, et al. “Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones.” Journal of the American Chemical Society, vol. 122, no. 51, Dec. 2000, pp. 12663-12674. https://doi.org/10.1021/ja003018i.