Nonheme iron(II) complexes of macrocyclic ligands in the generation of oxoiron(IV) complexes and the catalytic epoxidation of olefins

Yumi Suh, Mi Sook Seo, Kwan Mook Kim, Youn Sang Kim, Ho Gyeom Jang, Takehiko Tosha, Teizo Kitagawa, Jinheung Kim, Wonwoo Nam

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Mononuclear nonheme oxoiron(IV) complexes bearing 15-membered macrocyclic ligands were generated from the reactions of their corresponding iron(II) complexes and iodosylbenzene (PhIO) in CH3CN. The oxoiron(IV) species were characterized with various spectroscopic techniques such as UV-vis spectrophotometer, electron paramagnetic resonance, electrospray ionization mass spectrometer, and resonance Raman spectroscopy. The oxoiron(IV) complexes were inactive in olefin epoxidation. In contrast, when iron(II) or oxoiron(IV) complexes were combined with PhIO in the presence of olefins, high yields of epoxide products were obtained. These results indicate that in addition to the oxoiron(IV) species, there must be at least one more active oxidant (e.g., FeIV-OIPh adduct or oxoiron(V) species) that effects the olefin epoxidation. We have also demonstrated that the ligand environment of iron catalysts is an important factor in controlling the catalytic activity as well as the product selectivity in the epoxidation of olefins by PhIO.

Original languageEnglish
Pages (from-to)627-633
Number of pages7
JournalJournal of Inorganic Biochemistry
Issue number4
Publication statusPublished - 2006 Apr 1
Externally publishedYes



  • Biomimetic oxidation
  • Nonheme iron complex
  • Olefin epoxidation
  • Oxoiron(IV) intermediate
  • Oxygen activation

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

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