Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

Peter Spannring, Vital A. Yazerski, Jianming Chen, Matthias Otte, Bert M. Weckhuysen, Pieter C A Bruijnincx, Robertus J M Klein Gebbink*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

Original languageEnglish
Pages (from-to)3462-3466
Number of pages5
JournalEuropean Journal of Inorganic Chemistry
Volume2015
Issue number21
DOIs
Publication statusPublished - 1 Jul 2015

Keywords

  • Hydrogen peroxide
  • Iron
  • Olefin cleavage
  • Oxidation
  • Regioselectivity

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