Mononuclear Nonheme Iron(III)-Iodosylarene and High-Valent Iron-Oxo Complexes in Olefin Epoxidation Reactions

Bin Wang, Yong Min Lee, Mi Sook Seo, Wonwoo Nam

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

High-spin iron(III)-iodosylarene complexes are highly reactive in the epoxidation of olefins, in which epoxides are formed as the major products with high stereospecificity and enantioselectivity. The reactivity of the iron(III)-iodosylarene intermediates is much greater than that of the corresponding iron(IV)-oxo complex in these reactions. The iron(III)-iodosylarene species - not high-valent iron(IV)-oxo and iron(V)-oxo species - are also shown to be the active oxidants in catalytic olefin epoxidation reactions. The present results are discussed in light of the long-standing controversy on the one oxidant versus multiple oxidants hypothesis in oxidation reactions. On active duty: High-spin iron(III)-iodosylarene complexes epoxidize olefins with high stereospecificity and enantioselectivity. The iron(III)-iodosylarene species, not high-valent iron(IV)- and iron(V)-oxo species, are the active oxidants in catalytic olefin epoxidation reactions. The present results resolve the long-standing controversy on the one oxidant versus multiple oxidants hypothesis in oxidation reactions.

Original languageEnglish
Pages (from-to)11740-11744
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number40
DOIs
StatePublished - 1 Sep 2015

Keywords

  • bioinorganic chemistry
  • enzyme models
  • epoxidation
  • iron complexes
  • reaction mechanisms

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