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Synthesis and reactivity of ruthenium phosphite indenylidene complexes

Xavier Bantreil, Albert Poater, César A. Urbina-Blanco (UGent) , Yannick D Bidal, Laura Falivene, Rebecca AM Randall, Luigi Cavallo, Alexandra MZ Slawin and Catherine Cazin (UGent)
(2012) ORGANOMETALLICS. 31(21). p.7415-7426
Author
Organization
Abstract
The synthesis of the four olefin metathesis precatalysts Caz-1a-d, featuring the NHC ligand N,N'-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (SIMes) and four different phosphites (P((OPr)-Pr-i)(3), P(OPh)(3), P(OEt)(3), and P(OMe)(3)), is reported. The complexes are readily synthesized from commercially available [RuCl2(3-phenylinden-1-ylidene)-(pyridine)(SIMes)] (Ind-III) in yields of up to 88%. These complexes adopt an unusual cis configuration between the phosphite and the NHC ligands. NMR experiments and computational studies confirm that the cis complexes are thermodynamically favored in comparison to their trans counterparts. In addition, the isomerization from trans to cis occurs via a mononuclear and non-dissociative mechanism. Among the four precatalysts, cis-Caz-1a, featuring a P((OPr)-Pr-i)(3) ligand, displays the highest activity in ring-closing metathesis and cross-metathesis transformations. Experiments at low catalyst loadings demonstrated the potential of this catalyst, allowing better conversions than with commonly used commercially available precatalysts.
Keywords
RING-CLOSING METATHESIS, OLEFIN-METATHESIS CATALYSTS, N-HETEROCYCLIC CARBENE, LIGAND SUBSTITUTION ENERGIES, TRANSITION-METAL-COMPLEXES, NOBEL LECTURE 2005, DEMANDING NHC LIGAND, DISPERSIVE INTERACTIONS, DFT METHODS, ENYNE METATHESIS

Citation

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MLA
Bantreil, Xavier, et al. “Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes.” ORGANOMETALLICS, vol. 31, no. 21, 2012, pp. 7415–26, doi:10.1021/om300703p.
APA
Bantreil, X., Poater, A., Urbina-Blanco, C. A., Bidal, Y. D., Falivene, L., Randall, R. A., … Cazin, C. (2012). Synthesis and reactivity of ruthenium phosphite indenylidene complexes. ORGANOMETALLICS, 31(21), 7415–7426. https://doi.org/10.1021/om300703p
Chicago author-date
Bantreil, Xavier, Albert Poater, César A. Urbina-Blanco, Yannick D Bidal, Laura Falivene, Rebecca AM Randall, Luigi Cavallo, Alexandra MZ Slawin, and Catherine Cazin. 2012. “Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes.” ORGANOMETALLICS 31 (21): 7415–26. https://doi.org/10.1021/om300703p.
Chicago author-date (all authors)
Bantreil, Xavier, Albert Poater, César A. Urbina-Blanco, Yannick D Bidal, Laura Falivene, Rebecca AM Randall, Luigi Cavallo, Alexandra MZ Slawin, and Catherine Cazin. 2012. “Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes.” ORGANOMETALLICS 31 (21): 7415–7426. doi:10.1021/om300703p.
Vancouver
1.
Bantreil X, Poater A, Urbina-Blanco CA, Bidal YD, Falivene L, Randall RA, et al. Synthesis and reactivity of ruthenium phosphite indenylidene complexes. ORGANOMETALLICS. 2012;31(21):7415–26.
IEEE
[1]
X. Bantreil et al., “Synthesis and reactivity of ruthenium phosphite indenylidene complexes,” ORGANOMETALLICS, vol. 31, no. 21, pp. 7415–7426, 2012.
@article{8166484,
  abstract     = {{The synthesis of the four olefin metathesis precatalysts Caz-1a-d, featuring the NHC ligand N,N'-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (SIMes) and four different phosphites (P((OPr)-Pr-i)(3), P(OPh)(3), P(OEt)(3), and P(OMe)(3)), is reported. The complexes are readily synthesized from commercially available [RuCl2(3-phenylinden-1-ylidene)-(pyridine)(SIMes)] (Ind-III) in yields of up to 88%. These complexes adopt an unusual cis configuration between the phosphite and the NHC ligands. NMR experiments and computational studies confirm that the cis complexes are thermodynamically favored in comparison to their trans counterparts. In addition, the isomerization from trans to cis occurs via a mononuclear and non-dissociative mechanism. Among the four precatalysts, cis-Caz-1a, featuring a P((OPr)-Pr-i)(3) ligand, displays the highest activity in ring-closing metathesis and cross-metathesis transformations. Experiments at low catalyst loadings demonstrated the potential of this catalyst, allowing better conversions than with commonly used commercially available precatalysts.}},
  author       = {{Bantreil, Xavier and Poater, Albert and Urbina-Blanco, César A. and Bidal, Yannick D and Falivene, Laura and Randall, Rebecca AM and Cavallo, Luigi and Slawin, Alexandra MZ and Cazin, Catherine}},
  issn         = {{0276-7333}},
  journal      = {{ORGANOMETALLICS}},
  keywords     = {{RING-CLOSING METATHESIS,OLEFIN-METATHESIS CATALYSTS,N-HETEROCYCLIC CARBENE,LIGAND SUBSTITUTION ENERGIES,TRANSITION-METAL-COMPLEXES,NOBEL LECTURE 2005,DEMANDING NHC LIGAND,DISPERSIVE INTERACTIONS,DFT METHODS,ENYNE METATHESIS}},
  language     = {{eng}},
  number       = {{21}},
  pages        = {{7415--7426}},
  title        = {{Synthesis and reactivity of ruthenium phosphite indenylidene complexes}},
  url          = {{http://dx.doi.org/10.1021/om300703p}},
  volume       = {{31}},
  year         = {{2012}},
}
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