Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H2O2 systems

Michael R. Bukowski, Peter Comba, Achim Lienke, Christian Limberg, Carlos Lopez De Laorden, Rubén Mas-Ballesté, Michael Merz, Larry Que

Research output: Contribution to journalArticlepeer-review

130 Scopus citations

Abstract

(Chemical Equation Presented) Going ferryl: FeII complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H 2O2 in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L = bispidine ligand). An {FeIV=O} complex is postulated to be the oxidant, formed by the homolytic cleavage of the O-O bond of an {FeIII-OOH} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.

Original languageEnglish (US)
Pages (from-to)3446-3449
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number21
DOIs
StatePublished - May 19 2006

Keywords

  • Coordination chemistry
  • Dihydroxylation
  • Epoxidation
  • Homogeneous catalysis
  • Iron

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