Olefin-dependent discrimination between two nonheme HO-Fev=O tautomeric species in catalytic H2O2 epoxidations

Anna Company, Yan Feng, Mireia Güell, Xavi Ribas, Josep M. Luis, Lawrence Que, Miquel Costas

Research output: Contribution to journalArticle

67 Scopus citations

Abstract

A study was conducted to demonstrate olefin-dependent discrimination of two nonheme HO-Fev=O tautomeric species in catalytic H2O 2 epoxidations. Mechanistic studies were carried out under the condition of excess of olefin to minimize over-oxidation reactions and all reactions for the study were carried out under a N2 atmosphere to prevent auto-oxidation process due to presence of O2. It was observed that the diol/epoxide (D/E) ration for these reaction was dependent on the specific olefin and ranged from 3/2 (cyclooctene) to 6/1 (1-octene). The oxidation of cyclooctene using H218O2 revealed that only 28% of the oxygen atoms in the epoxide derived from H 2O2. Mechanistic results suggested that HO-Fe v=O oxidant need to be labeled before its reaction with substrates.

Original languageEnglish (US)
Pages (from-to)3359-3362
Number of pages4
JournalChemistry - A European Journal
Volume15
Issue number14
DOIs
StatePublished - Mar 23 2009

Keywords

  • Bioinorganic chemistry
  • Enzyme catalysis
  • Nonheme oxygenases
  • Oxidation
  • Reaction mechanisms

Fingerprint Dive into the research topics of 'Olefin-dependent discrimination between two nonheme HO-Fe<sup>v</sup>=O tautomeric species in catalytic H<sub>2</sub>O<sub>2</sub> epoxidations'. Together they form a unique fingerprint.

  • Cite this