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Chemodivergent metathesis of dienynes catalyzed by ruthenium-indenylidene complexes : an experimental and computational study

(2009) CHEMISTRY-A EUROPEAN JOURNAL. 15(39). p.10244-10254
Author
Organization
Abstract
A study on the enyne metathesis reaction leading to the formation cyclic compounds using ruthenium-indenylidene complexes is presented. Several 1,11-dien-6-ynes have been subjected to ruthenium metathesis cyclization by using ruthenium-indenylidene complexes hearing various phosphine and N-heterocyclic carbene (NHC) ligands. Interestingly. for some substrates chemodivergent metathesis occurs and is a function of the catalyst employed This led us to investigate the competing "enc-then-yne" of "yne-then-ene" reaction pathways apparently at play in these systems using both experimental observations and DFT calculations. Experimental and computational studies were found in good agreement and permit to conclude that for phosphine-containing catalysts. the "ene-then-yne" pathway is exclusively adopted. On the other hand. fur catalysts bearing NHC ligands, both pathways are possible.
Keywords
density functional calculations, enynes, homogeneous catalysis, metathesis, N-heterocycle carbenes, ruthenium, RING-CLOSING METATHESIS, N-HETEROCYCLIC CARBENE, OLEFIN METATHESIS, ENYNE METATHESIS, REARRANGEMENT METATHESIS, OPENING/CROSS-METATHESIS, LAURENCIA-MAJUSCULA, GRUBBS RUTHENIUM, CROSS-METATHESIS, NATURAL-PRODUCTS

Citation

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MLA
Clavier, Herve, et al. “Chemodivergent Metathesis of Dienynes Catalyzed by Ruthenium-Indenylidene Complexes : An Experimental and Computational Study.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 15, no. 39, 2009, pp. 10244–54.
APA
Clavier, H., Correa, A., Escudero-Adan, E. C., Benet-Buchholz, J., Cavallo, L., & Nolan, S. (2009). Chemodivergent metathesis of dienynes catalyzed by ruthenium-indenylidene complexes : an experimental and computational study. CHEMISTRY-A EUROPEAN JOURNAL, 15(39), 10244–10254.
Chicago author-date
Clavier, Herve, Andrea Correa, Eduardo C Escudero-Adan, Jordi Benet-Buchholz, Luigi Cavallo, and Steven Nolan. 2009. “Chemodivergent Metathesis of Dienynes Catalyzed by Ruthenium-Indenylidene Complexes : An Experimental and Computational Study.” CHEMISTRY-A EUROPEAN JOURNAL 15 (39): 10244–54.
Chicago author-date (all authors)
Clavier, Herve, Andrea Correa, Eduardo C Escudero-Adan, Jordi Benet-Buchholz, Luigi Cavallo, and Steven Nolan. 2009. “Chemodivergent Metathesis of Dienynes Catalyzed by Ruthenium-Indenylidene Complexes : An Experimental and Computational Study.” CHEMISTRY-A EUROPEAN JOURNAL 15 (39): 10244–10254.
Vancouver
1.
Clavier H, Correa A, Escudero-Adan EC, Benet-Buchholz J, Cavallo L, Nolan S. Chemodivergent metathesis of dienynes catalyzed by ruthenium-indenylidene complexes : an experimental and computational study. CHEMISTRY-A EUROPEAN JOURNAL. 2009;15(39):10244–54.
IEEE
[1]
H. Clavier, A. Correa, E. C. Escudero-Adan, J. Benet-Buchholz, L. Cavallo, and S. Nolan, “Chemodivergent metathesis of dienynes catalyzed by ruthenium-indenylidene complexes : an experimental and computational study,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 15, no. 39, pp. 10244–10254, 2009.
@article{8169553,
  abstract     = {A study on the enyne metathesis reaction leading to the formation cyclic compounds using ruthenium-indenylidene complexes is presented. Several 1,11-dien-6-ynes have been subjected to ruthenium metathesis cyclization by using ruthenium-indenylidene complexes hearing various phosphine and N-heterocyclic carbene (NHC) ligands. Interestingly. for some substrates chemodivergent metathesis occurs and is a function of the catalyst employed This led us to investigate the competing "enc-then-yne" of "yne-then-ene" reaction pathways apparently at play in these systems using both experimental observations and DFT calculations. Experimental and computational studies were found in good agreement and permit to conclude that for phosphine-containing catalysts. the "ene-then-yne" pathway is exclusively adopted. On the other hand. fur catalysts bearing NHC ligands, both pathways are possible.},
  author       = {Clavier, Herve and Correa, Andrea and Escudero-Adan, Eduardo C and Benet-Buchholz, Jordi and Cavallo, Luigi and Nolan, Steven},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {density functional calculations,enynes,homogeneous catalysis,metathesis,N-heterocycle carbenes,ruthenium,RING-CLOSING METATHESIS,N-HETEROCYCLIC CARBENE,OLEFIN METATHESIS,ENYNE METATHESIS,REARRANGEMENT METATHESIS,OPENING/CROSS-METATHESIS,LAURENCIA-MAJUSCULA,GRUBBS RUTHENIUM,CROSS-METATHESIS,NATURAL-PRODUCTS},
  language     = {eng},
  number       = {39},
  pages        = {10244--10254},
  title        = {Chemodivergent metathesis of dienynes catalyzed by ruthenium-indenylidene complexes : an experimental and computational study},
  url          = {http://dx.doi.org/10.1002/chem.200900976},
  volume       = {15},
  year         = {2009},
}

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