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Ruthenium–indenylidene complexes bearing saturated N-heterocyclic carbenes : synthesis and application in ring-closing metathesis reactions

Stijn Monsaert (UGent) , Els De Canck (UGent) , Renata Drozdzak, Pascal Van Der Voort (UGent) , Pieter Hendrickx (UGent) , José Martins (UGent) and Francis Verpoort (UGent)
(2010) NATO Science for Peace and Security, series A : chemistry and biology. p.31-38
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Abstract
The synthesis of complexes of the general formula Cl2Ru(SIMes)(L)(3-phenylinden-1-ylidene), 3a (L = PCy3), 3b (L = PPh3), 3c (L = py) and Cl2Ru(SIMe)(L)(3-phenylinden-1-ylidene), 4c (L = PCy3), 4b (L = PPh3), 4c (L = py) from commercially available Cl2Ru(PR3)(2)(3-phenylinden-1-ylidene), 2a (R = Cy), 2b (R = Ph), is reported, and the summed complexes proved to be useful catalysts for various ring-closing metathesis reactions. The catalytic data reported furthermore demonstrate that the substitution pattern of the N-aryl group has a definite influence on the activity of the second generation indenylidene catalysts for a given metathesis reaction, i.e. catalysts containing the SIMe-ligand showed improved initiation compared to the more robust SIMes substituted catalysts. A strong temperature effect was observed on all of the reactions tested. It is shown that complexes containing the SIMe-ligand display higher initiation efficiency then their corresponding SIMes analogues.
Keywords
Pyridine ligand, Indenylidene complexes, N-Heterocyclic carbenes, Ring-closing metathesis, Metathesis catalysts, Diethyl diallylmalonate

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Chicago
Monsaert, Stijn, Els De Canck, Renata Drozdzak, Pascal Van Der Voort, Pieter Hendrickx, José Martins, and Francis Verpoort. 2010. “Ruthenium–indenylidene Complexes Bearing Saturated N-heterocyclic Carbenes : Synthesis and Application in Ring-closing Metathesis Reactions.” In NATO Science for Peace and Security, Series A : Chemistry and Biology, ed. Valerian Dragutan, Albert Demonceau, Ileana Dragutan, and Eugene S Finkelshtein, 31–38. Dordrecht, The Netherlands: Springer.
APA
Monsaert, S., De Canck, E., Drozdzak, R., Van Der Voort, P., Hendrickx, P., Martins, J., & Verpoort, F. (2010). Ruthenium–indenylidene complexes bearing saturated N-heterocyclic carbenes : synthesis and application in ring-closing metathesis reactions. In V. Dragutan, A. Demonceau, I. Dragutan, & E. S. Finkelshtein (Eds.), NATO Science for Peace and Security, series A : chemistry and biology (pp. 31–38). Presented at the Conference of the NATO Advanced Study Institute on Green Metathesis Chemistry : great challenges in synthesis, catalysis and nanotechnology, Dordrecht, The Netherlands: Springer.
Vancouver
1.
Monsaert S, De Canck E, Drozdzak R, Van Der Voort P, Hendrickx P, Martins J, et al. Ruthenium–indenylidene complexes bearing saturated N-heterocyclic carbenes : synthesis and application in ring-closing metathesis reactions. In: Dragutan V, Demonceau A, Dragutan I, Finkelshtein ES, editors. NATO Science for Peace and Security, series A : chemistry and biology. Dordrecht, The Netherlands: Springer; 2010. p. 31–8.
MLA
Monsaert, Stijn, Els De Canck, Renata Drozdzak, et al. “Ruthenium–indenylidene Complexes Bearing Saturated N-heterocyclic Carbenes : Synthesis and Application in Ring-closing Metathesis Reactions.” NATO Science for Peace and Security, Series A : Chemistry and Biology. Ed. Valerian Dragutan et al. Dordrecht, The Netherlands: Springer, 2010. 31–38. Print.
@inproceedings{784804,
  abstract     = {The synthesis of complexes of the general formula Cl2Ru(SIMes)(L)(3-phenylinden-1-ylidene), 3a (L = PCy3), 3b (L = PPh3), 3c (L = py) and Cl2Ru(SIMe)(L)(3-phenylinden-1-ylidene), 4c (L = PCy3), 4b (L = PPh3), 4c (L = py) from commercially available Cl2Ru(PR3)(2)(3-phenylinden-1-ylidene), 2a (R = Cy), 2b (R = Ph), is reported, and the summed complexes proved to be useful catalysts for various ring-closing metathesis reactions. The catalytic data reported furthermore demonstrate that the substitution pattern of the N-aryl group has a definite influence on the activity of the second generation indenylidene catalysts for a given metathesis reaction, i.e. catalysts containing the SIMe-ligand showed improved initiation compared to the more robust SIMes substituted catalysts. A strong temperature effect was observed on all of the reactions tested. It is shown that complexes containing the SIMe-ligand display higher initiation efficiency then their corresponding SIMes analogues.},
  author       = {Monsaert, Stijn and De Canck, Els and Drozdzak, Renata and Van Der Voort, Pascal and Hendrickx, Pieter and Martins, Jos{\'e} and Verpoort, Francis},
  booktitle    = {NATO Science for Peace and Security, series A : chemistry and biology},
  editor       = {Dragutan, Valerian and Demonceau, Albert and Dragutan, Ileana and Finkelshtein, Eugene S},
  isbn         = {9789048134311},
  issn         = {1874-6489},
  keyword      = {Pyridine ligand,Indenylidene complexes,N-Heterocyclic carbenes,Ring-closing metathesis,Metathesis catalysts,Diethyl diallylmalonate},
  language     = {eng},
  location     = {Bucharest, Romania},
  pages        = {31--38},
  publisher    = {Springer},
  title        = {Ruthenium--indenylidene complexes bearing saturated N-heterocyclic carbenes : synthesis and application in ring-closing metathesis reactions},
  url          = {http://dx.doi.org/10.1007/978-90-481-3433-5\_3},
  year         = {2010},
}
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