Design of and mechanistic studies on a biomimetic iron-imidazole catalyst system for epoxidation of olefins with hydrogen peroxide

Kristin Schröder, Stephan Enthaler, Bianca Bitterlich, Thomas Schulz, Anke Spannenberg, Man Kin Tse, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

60 Scopus citations

Abstract

Novel iron catalysts, both defined and in situ generated, for the epoxidation of aromatic and aliphatic olefins with hydrogen peroxide as terminal oxidant are described. Our catalyst approach is based on bio-inspired 1-aryl-substituted imidazoles in combination with cheap and abundant iron trichloride hexahydrate. We show that the free 2-position of the imidazole ligand motif plays a key role for catalytic activity, as substitution leads to a dramatic depletion of yield and conversion. X-ray studies, UV/Vis titrations, and NMR studies were carried out to clarify the mechanism.

Original languageEnglish
Pages (from-to)5471-5481
Number of pages11
JournalChemistry - A European Journal
Volume15
Issue number22
DOIs
StatePublished - 25 May 2009
Externally publishedYes

Keywords

  • Epoxidation
  • Homogeneous catalysis
  • Iron
  • N ligands
  • Reaction mechanisms

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