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

Publication typeJournal Article
Publication date2000-12-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor15
ISSN00027863, 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...

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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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
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BibTex Copy
@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}
}
MLA
Cite this
MLA Copy
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.
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