Ionic liquid-assisted grinding: An electrophilic fluorination benchmark

Pavel A. Zaikin, Ok Ton Dyan, Innokenty R. Elanov, Gennady I. Borodkin

Research output: Contribution to journalArticlepeer-review

Abstract

We demonstrated the influence of liquid additives on the rate and selectivity of mechano-chemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichio-metric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.

Original languageEnglish
Article number5756
JournalMolecules
Volume26
Issue number19
DOIs
Publication statusPublished - 1 Oct 2021

Keywords

  • Aromatic substitution
  • Electrophilic substitution
  • Fluorine
  • Ionic liquids
  • Mechanochemistry
  • Solvent-free synthesis

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES

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