Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 25, Pages 4254-4265Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900407
Keywords
Boomerang catalysts; Metathesis; Carbene ligands; Heterocycles; Recycling; Ruthenium
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Funding
- European Community through the seventh framework program [CP-FP 211468-2 EUMET]
- Centre National de la Recherche Scientifique (CNRS)
- Region Bretagne
- Agence Nationale de la Recherche
- Ministere de la Recherche et de la Technologie
- Spanish Ministerio de Educacion y Ciencia (MEC)
- ICIQ Foundation
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The synthesis and characterization of three novel trifluoro-methylamido-conta-ming boomerang precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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