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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)2260-2263
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number15
DOIs
Publication statusPublished - 2020 Apr 23
Externally publishedYes

Keywords

  • Allylic compounds
  • Epoxidation
  • Hydrophobic effect
  • Sustainable chemistry
  • Zeolites

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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