The doping effect of fluorinated aromatic solvents on the rate of ruthenium-catalysed olefin metathesis

Cezary Samojłowicz, Michał Bieniek, Aleksandra Pazio, Anna Makal, Krzysztof Woźniak, Albert Poater, Luigi Cavallo, Jacek Wõjcik, Konrad Zdanowski, Karol Grela*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

A study concerning the effect of using a fluorinated aromatic solvent as the medium for olefin metathesis reactions catalysed by ruthenium complexes bearing N-heterocyclic carbene ligands is presented. The use of fluorinated aromatic hydrocarbons (FAH) as solvents for olefin metathesis reactions catalysed by standard commercially available ruthenium pre-catalysts allows substantially higher yields of the desired products to be obtained, especially in the case of demanding polyfunctional molecules, including natural and biologically active compounds. Interactions between the FAH and the second-generation ruthenium catalysts, which apparently improve the efficiency of the olefin metathesis transformation, have been studied by X-ray structure analysis and computations, as well as by carrying out a number of metathesis experiments. The optimisation of reaction conditions by using an FAH can be regarded as a complementary approach for the design of new improved ruthenium catalysts. Fluorinated aromatic solvents are an attractive alternative medium for promoting challenging olefin metathesis reactions. The solvent makes the difference: A remarkable enhancement of activity in catalytic olefin metathesis is observed when second-generation ruthenium pre-catalysts are applied in fluorinated aromatic solvents (see figure). In these media, challenging metathesis transformations, such as the formation of tetrasubstituted C-C double bonds, become possible with standard commercially available ruthenium pre-catalysts.

Original languageEnglish (US)
Pages (from-to)12981-12993
Number of pages13
JournalChemistry - A European Journal
Volume17
Issue number46
DOIs
StatePublished - Nov 11 2011

Keywords

  • N-heterocyclic carbenes
  • doping effects
  • fluorinated aromatic hydrocarbons
  • metathesis
  • ruthenium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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