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Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts

Baoyi Yu (UGent) , Zhixiong Luo (UGent) , Fatma B Hamad, Karen Leus (UGent) , Kristof Van Hecke (UGent) and Francis Verpoort (UGent)
(2016) CATALYSIS SCIENCE & TECHNOLOGY. 6(7). p.2092-2100
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Abstract
We report on the synthesis and characterization of a second generation of ruthenium catalysts bearing different sized indenylidene ligands, denoted as RuCl2(3-(2,6-xylyl)-1-indenylidene)(SIMes)(PCy3) 5a, RuCl2(4-methyl-3-(o-tolyl)-1-indenylidene)(SIMes)(PCy3) 5b, RuCl2(3-1-naphthyl-1-indenylidene)(SIMes)(PCy3) 5c and RuCl2(3-(p-fluorophenyl)-1-indenylidene)(SIMes)(PCy3) 5d. These complexes were characterized by NMR, IR, HRMS and elemental analysis. Moreover, the configurations of complexes 5a, 5b and 5d were confirmed by single-crystal X-ray diffraction analysis. The catalytic performances of complexes 5a-d were evaluated in several olefin metathesis reactions: the RCM of substrates 6 and 7, the RCEYM of substrate 8 and the ROMP of COD, in comparison with commercially available catalyst 3a. Careful analysis of the catalytic performances and single-crystal X-ray diffraction data of complexes 5a-5d reveal that the steric modification on the 3-phenyl group has a significant influence on the ligand congestion around the ruthenium center, altering the catalytic activity in metathesis reactions. In addition, the better-performing complex 5a was further investigated in the RCM of substrate 6 in comparison with complex 3c and benchmark complexes 1b, 2 and 3a.
Keywords
N-HETEROCYCLIC CARBENES, RING-CLOSING METATHESIS, COMPLEXES BEARING, IMIDAZOLIN-2-YLIDENE LIGANDS, NHC LIGAND, ALLENYLIDENE, IMIDAZOL(IN)IUM-2-CARBOXYLATES, PRECURSORS, REACTIVITY, MECHANISM

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Citation

Please use this url to cite or link to this publication:

MLA
Yu, Baoyi et al. “Effect of the Bulkiness of Indenylidene Moieties on the Catalytic Initiation and Efficiency of Second-generation Ruthenium-based Olefin Metathesis Catalysts.” CATALYSIS SCIENCE & TECHNOLOGY 6.7 (2016): 2092–2100. Print.
APA
Yu, B., Luo, Z., Hamad, F. B., Leus, K., Van Hecke, K., & Verpoort, F. (2016). Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts. CATALYSIS SCIENCE & TECHNOLOGY, 6(7), 2092–2100.
Chicago author-date
Yu, Baoyi, Zhixiong Luo, Fatma B Hamad, Karen Leus, Kristof Van Hecke, and Francis Verpoort. 2016. “Effect of the Bulkiness of Indenylidene Moieties on the Catalytic Initiation and Efficiency of Second-generation Ruthenium-based Olefin Metathesis Catalysts.” Catalysis Science & Technology 6 (7): 2092–2100.
Chicago author-date (all authors)
Yu, Baoyi, Zhixiong Luo, Fatma B Hamad, Karen Leus, Kristof Van Hecke, and Francis Verpoort. 2016. “Effect of the Bulkiness of Indenylidene Moieties on the Catalytic Initiation and Efficiency of Second-generation Ruthenium-based Olefin Metathesis Catalysts.” Catalysis Science & Technology 6 (7): 2092–2100.
Vancouver
1.
Yu B, Luo Z, Hamad FB, Leus K, Van Hecke K, Verpoort F. Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts. CATALYSIS SCIENCE & TECHNOLOGY. 2016;6(7):2092–100.
IEEE
[1]
B. Yu, Z. Luo, F. B. Hamad, K. Leus, K. Van Hecke, and F. Verpoort, “Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts,” CATALYSIS SCIENCE & TECHNOLOGY, vol. 6, no. 7, pp. 2092–2100, 2016.
@article{7203518,
  abstract     = {We report on the synthesis and characterization of a second generation of ruthenium catalysts bearing different sized indenylidene ligands, denoted as RuCl2(3-(2,6-xylyl)-1-indenylidene)(SIMes)(PCy3) 5a, RuCl2(4-methyl-3-(o-tolyl)-1-indenylidene)(SIMes)(PCy3) 5b, RuCl2(3-1-naphthyl-1-indenylidene)(SIMes)(PCy3) 5c and RuCl2(3-(p-fluorophenyl)-1-indenylidene)(SIMes)(PCy3) 5d. These complexes were characterized by NMR, IR, HRMS and elemental analysis. Moreover, the configurations of complexes 5a, 5b and 5d were confirmed by single-crystal X-ray diffraction analysis. The catalytic performances of complexes 5a-d were evaluated in several olefin metathesis reactions: the RCM of substrates 6 and 7, the RCEYM of substrate 8 and the ROMP of COD, in comparison with commercially available catalyst 3a. Careful analysis of the catalytic performances and single-crystal X-ray diffraction data of complexes 5a-5d reveal that the steric modification on the 3-phenyl group has a significant influence on the ligand congestion around the ruthenium center, altering the catalytic activity in metathesis reactions. In addition, the better-performing complex 5a was further investigated in the RCM of substrate 6 in comparison with complex 3c and benchmark complexes 1b, 2 and 3a.},
  author       = {Yu, Baoyi and Luo, Zhixiong and Hamad, Fatma B and Leus, Karen and Van Hecke, Kristof and Verpoort, Francis},
  issn         = {2044-4753},
  journal      = {CATALYSIS SCIENCE & TECHNOLOGY},
  keywords     = {N-HETEROCYCLIC CARBENES,RING-CLOSING METATHESIS,COMPLEXES BEARING,IMIDAZOLIN-2-YLIDENE LIGANDS,NHC LIGAND,ALLENYLIDENE,IMIDAZOL(IN)IUM-2-CARBOXYLATES,PRECURSORS,REACTIVITY,MECHANISM},
  language     = {eng},
  number       = {7},
  pages        = {2092--2100},
  title        = {Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts},
  url          = {http://dx.doi.org/10.1039/c5cy01506e},
  volume       = {6},
  year         = {2016},
}

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