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

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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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MLA
Monsaert, Stijn, 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, edited by Valerian Dragutan et al., Springer, 2010, pp. 31–38, doi:10.1007/978-90-481-3433-5_3.
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). https://doi.org/10.1007/978-90-481-3433-5_3
Chicago author-date
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, edited by Valerian Dragutan, Albert Demonceau, Ileana Dragutan, and Eugene S Finkelshtein, 31–38. Dordrecht, The Netherlands: Springer. https://doi.org/10.1007/978-90-481-3433-5_3.
Chicago author-date (all authors)
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 by. Valerian Dragutan, Albert Demonceau, Ileana Dragutan, and Eugene S Finkelshtein, 31–38. Dordrecht, The Netherlands: Springer. doi:10.1007/978-90-481-3433-5_3.
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.
IEEE
[1]
S. Monsaert et al., “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, Bucharest, Romania, 2010, pp. 31–38.
@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, José 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}},
  keywords     = {{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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