Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes

Herve Clavier, Frederic Caijo, Etienne Borre, Diane Rix, Fabien Boeda, Steven P. Nolan, Marc Mauduit

Research output: Contribution to journalArticlepeer-review

75 Citations (Scopus)

Abstract

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)

Original languageEnglish
Pages (from-to)4254-4265
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - Sept 2009

Keywords

  • Boomerang catalysts
  • Metathesis
  • Carbene ligands
  • Heterocycles
  • Recycling
  • Ruthenium
  • RING-CLOSING METATHESIS
  • TAGGED RUTHENIUM COMPLEXES
  • OLEFIN CROSS-METATHESIS
  • TETRASUBSTITUTED OLEFINS
  • NUCLEOPHILIC CARBENE
  • ALKENE METATHESIS
  • GRUBBS CATALYSTS
  • NEW-GENERATION
  • IONIC LIQUIDS
  • BEARING

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