Journal of the American Chemical Society, volume 126, issue 30, pages 9318-9325
Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation
Anna Michrowska
1
,
Robert Bujok
1
,
Syuzanna R. Harutyunyan
1
,
Volodymyr Sashuk
1
,
Grigory Dolgonos
1
,
1
Contribution from the Institutes of Organic Chemistry and Physical Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
|
Publication type: Journal Article
Publication date: 2004-07-13
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta- and para-substituted complexes are attractive from a practical point of view. These catalysts operate in very mild conditions and can be successfully applied in various types of metathesis [ring-closing metathesis, cross-metathesis (CM), and enyne metathesis]. Although the presence of a NO(2) group leads to catalysts that are dramatically more active than both the second-generation Grubbs's catalyst and the phosphine-free Hoveyda's carbene, enhancement of reactivity is somewhat lower than that observed for a sterically activated Hoveyda-Grubbs catalyst. Attempts to combine two modes of activation, steric and electronic, result in severely decreasing a catalyst's stability. The present findings illustrate that different Ru catalysts turned out to be optimal for different applications. Whereas phosphine-free carbenes are catalysts of choice for CM of various electron-deficient substrates, they exhibit lower reactivity in the formation of tetrasubstituted double bonds. This demonstrates that no single catalyst outperforms all others in all possible applications.
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Michrowska A. et al. Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation // Journal of the American Chemical Society. 2004. Vol. 126. No. 30. pp. 9318-9325.
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Michrowska A., Bujok R., Harutyunyan S. R., Sashuk V., Dolgonos G., Grela K. Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation // Journal of the American Chemical Society. 2004. Vol. 126. No. 30. pp. 9318-9325.
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RIS
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TY - JOUR
DO - 10.1021/ja048794v
UR - https://doi.org/10.1021/ja048794v
TI - Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation
T2 - Journal of the American Chemical Society
AU - Michrowska, Anna
AU - Bujok, Robert
AU - Dolgonos, Grigory
AU - Harutyunyan, Syuzanna R.
AU - Sashuk, Volodymyr
AU - Grela, Karol
PY - 2004
DA - 2004/07/13 00:00:00
PB - American Chemical Society (ACS)
SP - 9318-9325
IS - 30
VL - 126
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2004_Michrowska,
author = {Anna Michrowska and Robert Bujok and Grigory Dolgonos and Syuzanna R. Harutyunyan and Volodymyr Sashuk and Karol Grela},
title = {Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation},
journal = {Journal of the American Chemical Society},
year = {2004},
volume = {126},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/ja048794v},
number = {30},
pages = {9318--9325},
doi = {10.1021/ja048794v}
}
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Michrowska, Anna, et al. “Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes: Enhancement of Catalyst Activity through Electronic Activation.” Journal of the American Chemical Society, vol. 126, no. 30, Jul. 2004, pp. 9318-9325. https://doi.org/10.1021/ja048794v.