N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts
Publication type: Journal Article
Publication date: 2016-03-04
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
We report the synthesis of ruthenium metathesis catalysts containing unsymmetrical N-trifluoromethyl NHC ligands. These complexes have been fully characterized, and a Ru–F interaction has been identified in the solid state by X-ray crystallographic analysis for three catalysts with Ru–F distances between 2.629(2) and 2.652(2) A. The influence of the N-trifluoromethyl NHC ligands on the initiation rates and activation parameters was studied. The activity of these catalysts was evaluated in benchmark olefin metathesis reactions and compared to the standard second-generation Grubbs catalyst. Remarkably, N-trifluoromethyl catalysts display an unusually high selectivity for the formation of terminal olefins (up to 90%) in the ethenolysis of ethyl oleate. Much improved selectivity is demonstrated for alternating copolymerization of cyclooctene and norbornene as well. These results underline the importance of electronic effects exerted by the NHC ligand.
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Citations from 2024:
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GOST
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Engl P. S. et al. N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts // Organometallics. 2016. Vol. 35. No. 6. pp. 887-893.
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Engl P. S., Fedorov A., Copéret C., Togni A. N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts // Organometallics. 2016. Vol. 35. No. 6. pp. 887-893.
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RIS
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TY - JOUR
DO - 10.1021/acs.organomet.6b00028
UR - https://doi.org/10.1021/acs.organomet.6b00028
TI - N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts
T2 - Organometallics
AU - Engl, Pascal S
AU - Fedorov, Alexey
AU - Copéret, Christophe
AU - Togni, Antonio
PY - 2016
DA - 2016/03/04
PB - American Chemical Society (ACS)
SP - 887-893
IS - 6
VL - 35
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Engl,
author = {Pascal S Engl and Alexey Fedorov and Christophe Copéret and Antonio Togni},
title = {N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts},
journal = {Organometallics},
year = {2016},
volume = {35},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.organomet.6b00028},
number = {6},
pages = {887--893},
doi = {10.1021/acs.organomet.6b00028}
}
Cite this
MLA
Copy
Engl, Pascal S., et al. “N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts.” Organometallics, vol. 35, no. 6, Mar. 2016, pp. 887-893. https://doi.org/10.1021/acs.organomet.6b00028.