Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents

M. S. Yusubov, V. D. Filimonov, V. Vasilyeva, K. W. Chi

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

Original languageEnglish
Pages (from-to)1234-1236
Number of pages3
JournalSynthesis
Issue number10
DOIs
Publication statusPublished - 1 Jan 1995

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Dimethyl Sulfoxide
Benzene
Carbon
Oxidation

Keywords

  • 1,2-diketone
  • chemoselective oxidation
  • DMSO-based reagents
  • double or triple bond
  • Pd(II) catalyst

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents. / Yusubov, M. S.; Filimonov, V. D.; Vasilyeva, V.; Chi, K. W.

In: Synthesis, No. 10, 01.01.1995, p. 1234-1236.

Research output: Contribution to journalArticle

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AU - Vasilyeva, V.

AU - Chi, K. W.

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AB - HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

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KW - Pd(II) catalyst

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