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The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis
Author(s) -
Samojłowicz Cezary,
Bieniek Michał,
Pazio Aleksandra,
Makal Anna,
Woźniak Krzysztof,
Poater Albert,
Cavallo Luigi,
Wójcik Jacek,
Zdanowski Konrad,
Grela Karol
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100160
Subject(s) - ruthenium , carbene , metathesis , catalysis , olefin fiber , chemistry , ring opening metathesis polymerisation , olefin metathesis , acyclic diene metathesis , organic chemistry , salt metathesis reaction , combinatorial chemistry , polymerization , polymer
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.