Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

Wai Hung Cheung, Wing Ping Yip, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

10 Citations (Scopus)

Abstract

A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.
Original languageEnglish
Pages (from-to)521-526
Number of pages6
JournalCanadian Journal of Chemistry
Volume83
Issue number6-7
DOIs
Publication statusPublished - 1 Jun 2005
Externally publishedYes

Keywords

  • Oxidation
  • Quinones
  • Ruthenium catalyst
  • Tert-butyl hydroperoxide

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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