Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate

Yoshihiro Kon, Takuya Nakashima, Dachao Hong, Xinyi Ji, Ryota Osuga, Satoru Ito, Tadahiro Fujitani, Kazuhiko Sato, Toshiyuki Yokoi

研究成果: Article査読

抄録

The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.

本文言語English
ページ(範囲)2260-2263
ページ数4
ジャーナルEuropean Journal of Organic Chemistry
2020
15
DOI
出版ステータスPublished - 2020 4 23
外部発表はい

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

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