Beilstein J. Org. Chem.2024,20, 1278–1285, doi:10.3762/bjoc.20.110
Stefan Fritsch Thomas Strassner Physikalische Organische Chemie, Technische Universität Dresden, 01062 Dresden, Germany 10.3762/bjoc.20.110 Abstract We present a new class of tunable aryl alkyl ionic liquids (TAAILs) based on 1-aryl-4,5-dimethylimidazolium cations with electron-withdrawing and
. With an electrochemical window of up to 6.3 V, which is unprecedented for TAAILs with an NTf2 anion, this new class of TAAILs demonstrates the opportunities that arise from modifications in the backbone of the imidazolium cation.
Keywords: conductivity; electrochemical window; ionic liquids; tunable
introduced a new class of ionic liquids based on the 1-aryl-3-alkylimidazolium cation in 2009, the tunable aryl alkyl ionic liquids (TAAILs) [29]. This class of ionic liquids allows the modification of physical and chemical properties by variation of the functional groups present at the aryl ring of the
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Graphical Abstract
Scheme 1:
Overview of the synthesis of compounds 1–63.
Beilstein J. Org. Chem.2023,19, 212–216, doi:10.3762/bjoc.19.20
liquids (TAAILs) has been developed. Through optimization of the metal salt, reaction conditions and ionic liquids, we were able to design a robust catalyst system that tolerates different electron-rich substrates under ambient atmosphere and allows for a multigram scale.
Keywords: Friedel–Crafts
acylation; homogeneous catalysis; ionic liquids; iron catalysis; TAAILs; Introduction
The Friedel–Crafts acylation is one of the oldest metal-catalyzed reactions in organic chemistry [1] and allows for the synthesis of a broad range of diverse compounds [2][3][4][5]. Starting from electron-rich aromatic
cost-efficient metal salts in a water and air stable ionic liquid is still hard to find [50][51].
In this contribution, we present the use of imidazolium-based tunable aryl alkyl ionic liquids (TAAILs) in a catalytic Friedel–Crafts acylation. This relatively new class of ionic liquids [52] previously
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Graphical Abstract
Scheme 1:
Synthesis of TAAILs. i) 1 equiv glyoxal, 2.1 equiv formaldehyde, 2 equiv NH4Cl, MeOH, 65 °C, ii) 1....