Dihydroxylation of styrene by sodium chlorite with scandium triflate

Kei Ohkubo, Kensaku Hirose, Takekatsu Shibata, Kiyoto Takamori, Shunichi Fukuzumi

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8 Scopus citations

Abstract

Dihydroxylation of styrene by chlorite (ClO2 ) with scandium triflate [Sc(OTf)3] occurs efficiently to produce 1-phenylethane-1,2-diol under the ambient conditions. Scandium triflate acting as a strong Lewis acid is found to accelerate the disproportionation of ClO2 to produce ClO and ClO3 . A scandium-chlorine dioxide complex (Sc3+ClO2 ) is generated by the reaction of ClO with ClO2 in the presence of Sc3 +. The binding of Sc3 + to ClO2 was detected by the electron paramagnetic resonance measurements, enhancing the reactivity and selectivity of styrene hydroxylation.

Original languageEnglish
Article numbere3619
JournalJournal of Physical Organic Chemistry
Volume30
Issue number5
DOIs
StatePublished - 1 May 2017

Bibliographical note

Publisher Copyright:
Copyright © 2016 John Wiley & Sons, Ltd.

Keywords

  • Lewis acid
  • chlorine dioxide
  • chlorite
  • dihydroxylation
  • electron paramagnetic resonance

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