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N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts : a comparative study in Olefin metathesis

Herve Clavier and Steven Nolan UGent (2007) CHEMISTRY-A EUROPEAN JOURNAL. 13(28). p.8029-8036
abstract
Kinetic studies on ring-closing metathesis of unhindered and hindered substrates using phosphine and N-heterocyclic carbene (NHC)-containing ruthenium-indenylidene complexes (first and second generation precatalysts, respectively) have been carried out. These studies reveal an appealing difference, between the phosphine and NHC-containing catalysts, associated with a distinctive rate-determining step in the reaction mechanism. These catalysts have been compared with the benzylidene generation catalysts and their respective representative substrates. Finally, the reaction scope of the two most interesting precatalysts, complexes that contain tricyclohexylphosphine and 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (SIMes), has been investigated for the ring-closing and enyne metathesis for a large range of olefins. Owing to their high thermal stability, the SIMes-based indenylidene complexes were more efficient than their benzylidene analogues in the ring-closing metathesis of tetrasubstituted dienes. Importantly, none of the indenylidene precatalysts were found to be the most efficient for all of the substrates, indeed, a complementary complex-to-substrate activity relationship was observed.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
indenylidenes, metathesis, N-heterocyclic carbenes, phosphanes, ruthenium, RING-CLOSING METATHESIS, ENYNE METATHESIS, THEORETICAL PERSPECTIVE, GRUBBS CATALYSTS, 8-MEMBERED RINGS, COMPLEXES, EFFICIENT, MECHANISM, LIGANDS, CYCLIZATION
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
13
issue
28
pages
8029 - 8036
Web of Science type
Article
Web of Science id
000250032300021
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
5.33 (2007)
JCR rank
10/124 (2007)
JCR quartile
1 (2007)
ISSN
0947-6539
DOI
10.1002/chem.200700256
language
English
UGent publication?
no
classification
A1
id
8169869
handle
http://hdl.handle.net/1854/LU-8169869
date created
2016-11-24 15:56:30
date last changed
2018-01-29 12:12:29
@article{8169869,
  abstract     = {Kinetic studies on ring-closing metathesis of unhindered and hindered substrates using phosphine and N-heterocyclic carbene (NHC)-containing ruthenium-indenylidene complexes (first and second generation precatalysts, respectively) have been carried out. These studies reveal an appealing difference, between the phosphine and NHC-containing catalysts, associated with a distinctive rate-determining step in the reaction mechanism. These catalysts have been compared with the benzylidene generation catalysts and their respective representative substrates. Finally, the reaction scope of the two most interesting precatalysts, complexes that contain tricyclohexylphosphine and 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (SIMes), has been investigated for the ring-closing and enyne metathesis for a large range of olefins. Owing to their high thermal stability, the SIMes-based indenylidene complexes were more efficient than their benzylidene analogues in the ring-closing metathesis of tetrasubstituted dienes. Importantly, none of the indenylidene precatalysts were found to be the most efficient for all of the substrates, indeed, a complementary complex-to-substrate activity relationship was observed.},
  author       = {Clavier, Herve and Nolan, Steven},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {indenylidenes,metathesis,N-heterocyclic carbenes,phosphanes,ruthenium,RING-CLOSING METATHESIS,ENYNE METATHESIS,THEORETICAL PERSPECTIVE,GRUBBS CATALYSTS,8-MEMBERED RINGS,COMPLEXES,EFFICIENT,MECHANISM,LIGANDS,CYCLIZATION},
  language     = {eng},
  number       = {28},
  pages        = {8029--8036},
  title        = {N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts : a comparative study in Olefin metathesis},
  url          = {http://dx.doi.org/10.1002/chem.200700256},
  volume       = {13},
  year         = {2007},
}

Chicago
Clavier, Herve, and Steven Nolan. 2007. “N-heterocyclic Carbene and Phosphine Ruthenium Indenylidene Precatalysts : a Comparative Study in Olefin Metathesis.” Chemistry-a European Journal 13 (28): 8029–8036.
APA
Clavier, H., & Nolan, S. (2007). N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts : a comparative study in Olefin metathesis. CHEMISTRY-A EUROPEAN JOURNAL, 13(28), 8029–8036.
Vancouver
1.
Clavier H, Nolan S. N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts : a comparative study in Olefin metathesis. CHEMISTRY-A EUROPEAN JOURNAL. 2007;13(28):8029–36.
MLA
Clavier, Herve, and Steven Nolan. “N-heterocyclic Carbene and Phosphine Ruthenium Indenylidene Precatalysts : a Comparative Study in Olefin Metathesis.” CHEMISTRY-A EUROPEAN JOURNAL 13.28 (2007): 8029–8036. Print.