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Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 7, pp 1099–1105 | Cite as

Ruthenium–arene catalysts bearing N-heterocyclic carbene ligands for olefin cyclopropanation and metathesis

  • Michaël Méret
  • Anna M. Maj
  • Albert Demonceau
  • Lionel Delaude
Original Paper

Abstract

Ruthenium–arene complexes bearing N-heterocyclic carbene (NHC) ligands with the generic formula [RuCl2(p-cymene)(NHC)] are efficient catalyst precursors for the cyclopropanation of activated olefins with ethyl diazoacetate, and the cis/trans diastereoselectivity of the reaction markedly depends on the steric bulk of the NHC. The procedure was successfully applied to styrene, α-methylstyrene, and various other styrenic derivatives bearing electron-withdrawing or donating substituents on their aromatic rings. The reaction of unactivated internal or terminal alkenes was more sluggish, and the use of norbornene as a substrate afforded only olefin metathesis. Further investigation of the ring-opening metathesis polymerization of this strained cycloolefin in the presence of trimethylsilyldiazomethane led to high molecular weight polynorbornene whose microstructure was not significantly affected by the choice of the NHC ancillary ligand.

Graphical abstract

Keywords

Arene complexes Cross-metathesis para-Cymene Homogeneous catalysis Ring-opening metathesis polymerization Structure–activity relationships 

Notes

Acknowledgments

The financial support of the “Fonds de la Recherche Scientifique-FNRS,” Brussels, is gratefully acknowledged.

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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Michaël Méret
    • 1
    • 2
  • Anna M. Maj
    • 1
    • 3
  • Albert Demonceau
    • 1
  • Lionel Delaude
    • 1
  1. 1.Laboratory of Organometallic Chemistry and Homogeneous Catalysis, Institut de Chimie (B6a)Université de LiègeLiègeBelgium
  2. 2.Max Planck Institute of Molecular Plant PhysiologyPotsdamGermany
  3. 3.Ecole Nationale Supérieure de Chimie de LilleVilleneuve d’AscqFrance

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