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New indenylidene-Schiff base-ruthenium complexes for cross-metathesis and ring-closing metathesis

Ana Lozano Vila (UGent) , Stijn Monsaert (UGent) , Renata Drozdzak, Stanislaw Wolowiec and Francis Verpoort (UGent)
(2009) ADVANCED SYNTHESIS & CATALYSIS. 351(16). p.2689-2701
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Abstract
We here report on the stability and catalytic activity of new indenylidene-Schiff base-ruthenium complexes 3a-f through representative cross-metathesis (CM) and ring-closing metathesis (RCM) reactions. Excellent activity of the new complexes was found for the two selected RCM reactions; prominent conversion was obtained compared to the commercial Hoveyda-Grubbs catalyst 2. Moreover, excellent results were obtained for a standard CM reaction. Higher conversions were achieved with one of the indenylidene catalysts compared with Hoveyda-Grubbs catalyst. Unexpectedly, an isomerization reaction was observed during the CM reaction of allylbenzene. To the best of our knowledge, isomerization reactions in this model CM reaction in closed systems have never been described using first generation catalysts, including the Hoveyda-Grubbs catalyst. The first model CM reactions as well as the RCM reactions have been monitored using H-1 NMR. The course of the CM reaction of 3-phenylprop-1-ene (8) and cis-1,4-diacetoxybut-2-ene(9) was monitored by GC. The isomerization reaction was studied by means of GC-mass spectrometry and in situ IR spectroscopy. All catalysts were structurally characterized by means of H-1, C-13, and P-31 NMR spectroscopy.
Keywords
indenylidenes, ring-closing metathesis, carbene ligands, cross-metathesis, ruthenium, Schiff bases, ELECTRON-WITHDRAWING LIGANDS, N-HETEROCYCLIC CARBENES, OLEFIN METATHESIS, GRUBBS CATALYSTS, PYRROLE SYNTHESIS, POLYMERIZATION, 1, 3-DIMESITYL-4, 5-DIHYDROIMIDAZOL-2-YLIDENE, RUCL2(=CHR)(PR(3))(2), COMBINATION, INITIATORS

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Citation

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MLA
Lozano Vila, Ana, et al. “New Indenylidene-Schiff Base-Ruthenium Complexes for Cross-Metathesis and Ring-Closing Metathesis.” ADVANCED SYNTHESIS & CATALYSIS, vol. 351, no. 16, 2009, pp. 2689–701, doi:10.1002/adsc.200900477.
APA
Lozano Vila, A., Monsaert, S., Drozdzak, R., Wolowiec, S., & Verpoort, F. (2009). New indenylidene-Schiff base-ruthenium complexes for cross-metathesis and ring-closing metathesis. ADVANCED SYNTHESIS & CATALYSIS, 351(16), 2689–2701. https://doi.org/10.1002/adsc.200900477
Chicago author-date
Lozano Vila, Ana, Stijn Monsaert, Renata Drozdzak, Stanislaw Wolowiec, and Francis Verpoort. 2009. “New Indenylidene-Schiff Base-Ruthenium Complexes for Cross-Metathesis and Ring-Closing Metathesis.” ADVANCED SYNTHESIS & CATALYSIS 351 (16): 2689–2701. https://doi.org/10.1002/adsc.200900477.
Chicago author-date (all authors)
Lozano Vila, Ana, Stijn Monsaert, Renata Drozdzak, Stanislaw Wolowiec, and Francis Verpoort. 2009. “New Indenylidene-Schiff Base-Ruthenium Complexes for Cross-Metathesis and Ring-Closing Metathesis.” ADVANCED SYNTHESIS & CATALYSIS 351 (16): 2689–2701. doi:10.1002/adsc.200900477.
Vancouver
1.
Lozano Vila A, Monsaert S, Drozdzak R, Wolowiec S, Verpoort F. New indenylidene-Schiff base-ruthenium complexes for cross-metathesis and ring-closing metathesis. ADVANCED SYNTHESIS & CATALYSIS. 2009;351(16):2689–701.
IEEE
[1]
A. Lozano Vila, S. Monsaert, R. Drozdzak, S. Wolowiec, and F. Verpoort, “New indenylidene-Schiff base-ruthenium complexes for cross-metathesis and ring-closing metathesis,” ADVANCED SYNTHESIS & CATALYSIS, vol. 351, no. 16, pp. 2689–2701, 2009.
@article{976401,
  abstract     = {{We here report on the stability and catalytic activity of new indenylidene-Schiff base-ruthenium complexes 3a-f through representative cross-metathesis (CM) and ring-closing metathesis (RCM) reactions. Excellent activity of the new complexes was found for the two selected RCM reactions; prominent conversion was obtained compared to the commercial Hoveyda-Grubbs catalyst 2. Moreover, excellent results were obtained for a standard CM reaction. Higher conversions were achieved with one of the indenylidene catalysts compared with Hoveyda-Grubbs catalyst. Unexpectedly, an isomerization reaction was observed during the CM reaction of allylbenzene. To the best of our knowledge, isomerization reactions in this model CM reaction in closed systems have never been described using first generation catalysts, including the Hoveyda-Grubbs catalyst. The first model CM reactions as well as the RCM reactions have been monitored using H-1 NMR. The course of the CM reaction of 3-phenylprop-1-ene (8) and cis-1,4-diacetoxybut-2-ene(9) was monitored by GC. The isomerization reaction was studied by means of GC-mass spectrometry and in situ IR spectroscopy. All catalysts were structurally characterized by means of H-1, C-13, and P-31 NMR spectroscopy.}},
  author       = {{Lozano Vila, Ana and Monsaert, Stijn and Drozdzak, Renata and Wolowiec, Stanislaw and Verpoort, Francis}},
  issn         = {{1615-4150}},
  journal      = {{ADVANCED SYNTHESIS & CATALYSIS}},
  keywords     = {{indenylidenes,ring-closing metathesis,carbene ligands,cross-metathesis,ruthenium,Schiff bases,ELECTRON-WITHDRAWING LIGANDS,N-HETEROCYCLIC CARBENES,OLEFIN METATHESIS,GRUBBS CATALYSTS,PYRROLE SYNTHESIS,POLYMERIZATION,1,3-DIMESITYL-4,5-DIHYDROIMIDAZOL-2-YLIDENE,RUCL2(=CHR)(PR(3))(2),COMBINATION,INITIATORS}},
  language     = {{eng}},
  number       = {{16}},
  pages        = {{2689--2701}},
  title        = {{New indenylidene-Schiff base-ruthenium complexes for cross-metathesis and ring-closing metathesis}},
  url          = {{http://doi.org/10.1002/adsc.200900477}},
  volume       = {{351}},
  year         = {{2009}},
}
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