Dihydroxylation of styrene by sodium chlorite with scandium triflate

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

doi:10.1002/poc.3619

Dihydroxylation of styrene by sodium chlorite with scandium triflate

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Article number	e3619
Journal	Journal of Physical Organic Chemistry
Volume	30
Issue number	5
DOIs	https://doi.org/10.1002/poc.3619
State	Published - 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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10.1002/poc.3619

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title = "Dihydroxylation of styrene by sodium chlorite with scandium triflate",

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.",

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T1 - Dihydroxylation of styrene by sodium chlorite with scandium triflate

AU - Ohkubo, Kei

AU - Hirose, Kensaku

AU - Shibata, Takekatsu

AU - Takamori, Kiyoto

AU - Fukuzumi, Shunichi

PY - 2017/5/1

Y1 - 2017/5/1

N2 - 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.

AB - 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.

KW - Lewis acid

KW - chlorine dioxide

KW - chlorite

KW - dihydroxylation

KW - electron paramagnetic resonance

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ER -

Dihydroxylation of styrene by sodium chlorite with scandium triflate

Abstract

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Keywords

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