One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst

Molecules. 2017 Aug 28;22(9):1385. doi: 10.3390/molecules22091385.

Abstract

In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF₄) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of the desired γ-lactones were directly prepared with high regioselectivities and yields in a simple one-pot procedure using [DMIM]F as Si-O bond activator and [Hbim]BF₄ as solvent and acidic ionic liquid catalyst. The ionic liquid mixture was recovered and reused three times and no loss in its activity was observed.

Keywords: catalyst; flourous ionic liquid; one-pot synthesis; regioselective; γ-lactone.

MeSH terms

  • Acetals / chemistry*
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Ethylenes / chemistry
  • Fluorides / chemistry*
  • Green Chemistry Technology
  • Imidazoles / chemistry
  • Ketones / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • 1,3-dimethylimidazolium
  • Acetals
  • Epoxy Compounds
  • Ethylenes
  • Imidazoles
  • Ketones
  • Lactones
  • ketene
  • Fluorides