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  Comparative Investigation of Ruthenium-Based Metathesis Catalysts Bearing N-Heterocyclic Carbene (NHC) Ligands

Fürstner, A., Ackermann, L., Gabor, B., Goddard, R., Lehmann, C. W., Mynott, R., et al. (2001). Comparative Investigation of Ruthenium-Based Metathesis Catalysts Bearing N-Heterocyclic Carbene (NHC) Ligands. Chemistry - A European Journal, 7(15), 3236-3253. doi:10.1002/1521-3765(20010803)7:15<3236:AID-CHEM3236>3.0.CO;2-S.

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 Creators:
Fürstner, Alois1, Author           
Ackermann, Lutz1, Author           
Gabor, Barbara2, Author           
Goddard, Richard3, Author           
Lehmann, Christian W.3, Author           
Mynott, Richard2, Author           
Stelzer, Frank1, Author           
Thiel, Oliver R.1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: carbenes; imidazol-2-ylidenes; IR thermography; metathesis; ruthenium
 Abstract: Exchange of one PCy3 unit of the classical Grubbs catalyst 1 by N-heterocyclic carbene (NHC) ligands leads to “second-generation” metathesis catalysts of superior reactivity and increased stability. Several complexes of this type have been prepared and fully characterized, six of them by X-ray crystallography. These include the unique chelate complexes 13 and 14 in which the NHC- and the Ru=CR entities are tethered to form a metallacycle. A particularly favorable design feature is that the reactivity of such catalysts can be easily adjusted by changing the electronic and steric properties of the NHC ligands. The catalytic activity also strongly depends on the solvent used; NMR investigations provide a tentative explanation of this effect. Applications of the “second-generation” catalysts to ring closing alkene metathesis and intramolecular enyne cycloisomerization reactions provide insights into their catalytic performance. From these comparative studies it is deduced that no single catalyst is optimal for different types of applications. The search for the most reactive catalyst for a specific transformation is facilitated by IR thermography allowing a rapid and semi-quantitative ranking among a given set of catalysts.

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Language(s): eng - English
 Dates: 2001-02-122001-07-172001-08-03
 Publication Status: Published in print
 Pages: 18
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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Title: Chemistry - A European Journal
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 18 Volume / Issue: 7 (15) Sequence Number: - Start / End Page: 3236 - 3253 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058