An air- and water-stable iodonium salt promoter for facile thioglycoside activation

Org Lett. 2014 Mar 21;16(6):1780-2. doi: 10.1021/ol5004059. Epub 2014 Mar 5.


The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68-97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background to construct glycosidic linkages.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Air
  • Gases
  • Glycosylation
  • Mesylates
  • Molecular Structure
  • Stereoisomerism
  • Thioglycosides / chemistry*
  • Water


  • Gases
  • Mesylates
  • Thioglycosides
  • Water