Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds

Mekhman S. Yusubov, Ki Whan Chi, Joo Yeon Park, Rashad Karimov, Viktor Vladimirovich Zhdankin

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51 Citations (Scopus)

Abstract

(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.

Original languageEnglish
Pages (from-to)6305-6308
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number35
DOIs
Publication statusPublished - 28 Aug 2006

Keywords

  • (Diacetoxyiodo)benzene
  • Catalysis
  • Hypervalent iodine
  • Iodylbenzene
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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