Saccharin-based μ-oxo imidoiodane: A readily available and highly reactive reagent for electrophilic amination

Akira Yoshimura, Steven R. Koski, Jonathan M. Fuchs, Akio Saito, Victor N. Nemykin, Viktor V. Zhdankin

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Three new saccharin-based hypervalent iodine compounds were prepared by the reaction of saccharine with (diacetoxyiodo)arenes or acetoxybenziodoxole. Structures of these new imidoiodanes were established by X-ray crystallography. The saccharin-based μ-oxo-bridged imidoiodane readily reacts with silyl enol ethers under mild conditions to give the corresponding α-aminated carbonyl compounds in moderate yields. Sweet saccharin: Three new saccharin-derived hypervalent iodine compounds were prepared by the reaction of saccharine with (diacetoxyiodo)arenes or acetoxybenziodoxole. The saccharin-based μ-oxo-bridged imidoiodane readily reacts with silyl enol ethers to give the corresponding α-aminated carbonyl compounds in moderate yields.

Original languageEnglish
Pages (from-to)5328-5331
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number14
DOIs
Publication statusPublished - 27 Mar 2015
Externally publishedYes

Fingerprint

Iodine compounds
Amination
Saccharin
Carbonyl compounds
Ethers
Iodine Compounds
X ray crystallography

Keywords

  • amination
  • hypervalent
  • iodine
  • oxidation
  • saccharin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Saccharin-based μ-oxo imidoiodane : A readily available and highly reactive reagent for electrophilic amination. / Yoshimura, Akira; Koski, Steven R.; Fuchs, Jonathan M.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.

In: Chemistry - A European Journal, Vol. 21, No. 14, 27.03.2015, p. 5328-5331.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Koski, Steven R. ; Fuchs, Jonathan M. ; Saito, Akio ; Nemykin, Victor N. ; Zhdankin, Viktor V. / Saccharin-based μ-oxo imidoiodane : A readily available and highly reactive reagent for electrophilic amination. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 14. pp. 5328-5331.
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