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

22 Scopus citations

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 (US)
Pages (from-to)5328-5331
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number14
DOIs
StatePublished - Mar 27 2015

Keywords

  • amination
  • hypervalent
  • iodine
  • oxidation
  • saccharin

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