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Increased efficiency in cross-metathesis reactions of sterically hindered olefins.
Org Lett. 2008 Feb 07; 10(3):441-4.OL

Abstract

Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is more efficient using the N-mesityl-containing catalyst. A hypothesis to explain this dichotomy is described.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Stewart IC
The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Douglas CJ
No affiliation info available
Grubbs RH
No affiliation info available

MeSH

AlkenesCatalysisHeterocyclic CompoundsHydrocarbonsMethaneModels, MolecularMolecular StructureOrganometallic CompoundsRuthenium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

18177048

Citation

Stewart, Ian C., et al. "Increased Efficiency in Cross-metathesis Reactions of Sterically Hindered Olefins." Organic Letters, vol. 10, no. 3, 2008, pp. 441-4.
Stewart IC, Douglas CJ, Grubbs RH. Increased efficiency in cross-metathesis reactions of sterically hindered olefins. Org Lett. 2008;10(3):441-4.
Stewart, I. C., Douglas, C. J., & Grubbs, R. H. (2008). Increased efficiency in cross-metathesis reactions of sterically hindered olefins. Organic Letters, 10(3), 441-4. https://doi.org/10.1021/ol702624n
Stewart IC, Douglas CJ, Grubbs RH. Increased Efficiency in Cross-metathesis Reactions of Sterically Hindered Olefins. Org Lett. 2008 Feb 7;10(3):441-4. PubMed PMID: 18177048.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Increased efficiency in cross-metathesis reactions of sterically hindered olefins. AU - Stewart,Ian C, AU - Douglas,Christopher J, AU - Grubbs,Robert H, Y1 - 2008/01/05/ PY - 2008/1/8/pubmed PY - 2008/4/12/medline PY - 2008/1/8/entrez SP - 441 EP - 4 JF - Organic letters JO - Org Lett VL - 10 IS - 3 N2 - Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is more efficient using the N-mesityl-containing catalyst. A hypothesis to explain this dichotomy is described. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18177048/Increased_efficiency_in_cross_metathesis_reactions_of_sterically_hindered_olefins_ DB - PRIME DP - Unbound Medicine ER -