Frontiers in Chemistry (Nov 2018)

Water-Tolerant Trifloaluminate Ionic Liquids: New and Unique Lewis Acidic Catalysts for the Synthesis of Chromane

  • Piotr Latos,
  • Alice Culkin,
  • Natalia Barteczko,
  • Sławomir Boncel,
  • Sebastian Jurczyk,
  • Lucy C. Brown,
  • Peter Nockemann,
  • Anna Chrobok,
  • Małgorzata Swadźba-Kwaśny

DOI
https://doi.org/10.3389/fchem.2018.00535
Journal volume & issue
Vol. 6

Abstract

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The first example of triflometallate ionic liquids, named in analogy to chlorometallate ionic liquids, is reported. Trifloaluminate ionic liquids, synthesized from 1-alkyl-3-methylimidazolium triflates and aluminum triflate, were characterized by multinuclear NMR spectroscopy and FT-IR spectroscopy, revealing the existence of oligonuclear, multiply-charged trifloaluminate anions, with multiple bridging triflate modes. Acceptor numbers were determined to quantify their Lewis acidity, rendering trifloaluminate ionic liquids as medium-strength Lewis acids (AN = ca. 65). Used as acidic catalysts in the cycloaddition of 2,4-dimethylphenol and isoprene (molar ratio 2:1) to prepare chromane, trifloaluminate systems outperformed literature systems, showing high activity (conversions 94–99%, selectivities 80–89%) and at low loadings (0.2 mol%) at 35°C. Using these new systems as supported ionic liquid phase (SILP) on multi-walled carbon nanotubes (ionic liquid loading 16 wt%) delivered a recyclable catalytic system, with activity enhanced with respect to the homogenous regime.

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