Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone® as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.

Original languageEnglish
Pages (from-to)5745-5752
Number of pages8
JournalTetrahedron
Volume66
Issue number31
DOIs
Publication statusPublished - 31 Jul 2010

Fingerprint

Iodine
Transition metals
Metals
Oxidants
Oxidation
Metalloporphyrins
Aromatic Hydrocarbons
Carbonyl compounds
Catalytic oxidation
Hydrocarbons
Sulfates
Alcohols
Substrates
iodosobenzene
potassium peroxymonosulfuric acid

Keywords

  • Catalysis
  • Hypervalent iodine
  • Oxidation
  • Porphyrins
  • Ruthenium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species. / Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor Vladimirovich.

In: Tetrahedron, Vol. 66, No. 31, 31.07.2010, p. 5745-5752.

Research output: Contribution to journalArticle

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