Organometallics, volume 30, issue 15, pages 4144-4158
Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench
Michał Bieniek
1
,
Cezary Samojłowicz
1
,
Volodymyr Sashuk
1
,
Robert Bujok
1
,
Paweł Śledź
1
,
Noël Lugan
2
,
Guy Lavigne
2
,
Dieter Arlt
3
,
1
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
|
2
Laboratoire de Chimie de Coordination du CNRS, 205 Route de Narbonne, 31077 Toulouse cedex 4, France
|
Publication type: Journal Article
Publication date: 2011-07-11
Journal:
Organometallics
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The series of upgraded Grubbs/Hoveyda second-generation catalysts (H2IMes)(Cl)2Ru═C(H)(C6H4OR) (E2 (71% yield), R = CH(Me)(C(O)OMe); M2 (58% yield), R = CH(C(O)OMe)2; Kme2 (88% yield), R = CH2C(O)Me; Ket2 (63% yield), R = CH2C(O)Et); C2 (58% yield), R = C(Me)CN) were prepared by the reaction of the Grubbs second-generation catalyst (H2IMes)(Cl)2Ru(CHPh)(PCy3) (G2) with the appropriate ortho-substituted ether H(Me)C═CHC6H4OR in the presence of CuCl as a phosphine scavenger. The X-ray structures of these complexes reveal that the terminal oxygen of the ester, ketone, or malonate group installed as the terminal substituent of the benzylidene ether is coordinated to the metal, giving an octahedral structure. In contrast, the nitrile group of the complex C2 remains uncoordinated. Even more sophisticated complexes, incorporating both a coordinating group R (ester or ketone) as a terminal substituent of the ether and an electron-withdrawing group X (NO2 or C(O)Me) on the aromatic ring, were synthesized: (H2IMes)...
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25
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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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Bieniek M. et al. Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench // Organometallics. 2011. Vol. 30. No. 15. pp. 4144-4158.
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Bieniek M., Samojłowicz C., Sashuk V., Bujok R., Śledź P., Lugan N., Lavigne G., Arlt D., Grela K. Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench // Organometallics. 2011. Vol. 30. No. 15. pp. 4144-4158.
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TY - JOUR
DO - 10.1021/om200463u
UR - https://doi.org/10.1021/om200463u
TI - Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench
T2 - Organometallics
AU - Bieniek, Michał
AU - Samojłowicz, Cezary
AU - Śledź, Paweł
AU - Lugan, Noël
AU - Lavigne, Guy
AU - Arlt, Dieter
AU - Sashuk, Volodymyr
AU - Bujok, Robert
AU - Grela, Karol
PY - 2011
DA - 2011/07/11 00:00:00
PB - American Chemical Society (ACS)
SP - 4144-4158
IS - 15
VL - 30
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2011_Bieniek,
author = {Michał Bieniek and Cezary Samojłowicz and Paweł Śledź and Noël Lugan and Guy Lavigne and Dieter Arlt and Volodymyr Sashuk and Robert Bujok and Karol Grela},
title = {Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench},
journal = {Organometallics},
year = {2011},
volume = {30},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/om200463u},
number = {15},
pages = {4144--4158},
doi = {10.1021/om200463u}
}
Cite this
MLA
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Bieniek, Michał, et al. “Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench.” Organometallics, vol. 30, no. 15, Jul. 2011, pp. 4144-4158. https://doi.org/10.1021/om200463u.