Application of halide molten salts as novel reaction media for O-glycosidic bond formation

Vineet Kumar, Ian Jamie Talisman, Sanjay V. Malhotra

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

In this study we have explored the application of halide molten salts as reaction media for O-glycosidic bond formation under basic conditions and mild heating. Eighteen different room-temperature ionic liquids and molten salts, representing four different classes of cations (i.e. imidazolium, pyridinium, pyrrolidinium and ammonium), were screened in the glycosidation reaction of p-nitrophenol with aceto-bromo-α-D-galactose. 1-Butyl-4-methylimidazolium chloride (BMIM·Cl) gave the best results and was applied in the reactions of other phenolic substrates to give the products with up to 80% yields. All the reactions were highly selective to give the β-anomers, and the molten salt BMIM·Cl could easily be reused with no apparent loss in activity.

Original languageEnglish (US)
Pages (from-to)3377-3381
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number18
DOIs
StatePublished - Jun 2010
Externally publishedYes

Keywords

  • Carbohydrates
  • Ionic liquids
  • Koenigs-Knorr reaction
  • Molten salts
  • O-Glycosidation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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