Synthesis of Chiral Ionic Liquids from Natural Monosaccharides

Abstract

Three series of new ionic liquids (ILs), namely imidazolium‐, pyrazolium‐, and bis‐benzimidazolium‐containing ILs, were prepared from low‐cost, unprotected carbohydrates. Information on anion‐cation interactions and solvation shell were obtained via diffusion NMR and heteronuclear Overhauser correlation maps (HOESY), respectively.

Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products

“…Moreover, their cytotoxicity and mutagenic activities were also evaluated. 38 A totally different approach to sugar-based ionic liquids was proposed 39 in 2022 by Marra, Mele, and their co-workers. They described the synthesis of imidazolium, pyrazolium, and bis-benzimidazolium ILs directly from simple, unprotected monosaccharides, instead of linking the nitrogenated heterocycles (e.g., imidazole) to a suitably functionalized carbohydrate or using an amino sugar (e.g., D-glucosamine 11) as starting material.…”

“…Conventional alkylation in the presence of iodomethane or 1-bromooctane led to the corresponding Omethylated or O-octylated derivatives that were then Nmethylated with methyl triflate to give ILs 73 and 74. 39 The application of the same synthetic approach to Dglucose 75 allowed the preparation of the two pyrazolium ILs 76 and 77 (Scheme 21). On the other hand, changing the protection of the vicinal diol from O-alkyl to O-isopropylidene gave access to the free-OH ionic liquid 78 and the fully O-protected ILs 79 and 80.…”

Synthesis and physical properties of tunable aryl alkyl ionic liquids based on 1-aryl-4,5-dimethylimidazolium cations

“…Ionic liquids (ILs) are a special class of solvents generally defined as salts with melting points below 100 °C [1]. Due to their unique properties, e.g., their high thermal stability and their negligible vapor pressure [2,3], ILs have found widespread use in different fields of chemistry like synthesis [4][5][6][7][8][9], catalysis [10][11][12][13][14] and materials science [15][16][17][18][19][20][21][22][23]. ILs generally consist of an organic cation [24], such as the imidazolium or ammonium ion and an inorganic anion like a halide anion or weakly coordinating anions like bis(trifluoromethylsulfonyl)imide [NTf 2 ] − [25].…”

Scope and Limitations in the Synthesis of Glucosamine‐based Ionic Liquids

“…Overall carbohydrate based ionic liquids have been synthesized from many different sugars, most commonly from glucose, [7–8,10–11,13–14,16–17] but also from galactose, [12] ribose, [9,14,25] xylose, [18] isomannide, [19] isosorbide [20–21] and linear sugars [22] among others. Many of these aforementioned carbohydrate based ionic liquids follow the overall same synthetic strategy: First, a for the carbohydrate of choice (e. g. glucose, galactose, ribose, etc.)…”

“…[13] Carbohydrate based ionic liquids [14] are of increased interest in comparison to common imidazolium-based ionic liquids due to their biomass origin and their heightened biocompatibility. [15] Overall carbohydrate based ionic liquids have been synthesized from many different sugars, most commonly from glucose, [7][8][10][11][13][14][16][17] but also from galactose, [12] ribose, [9,14,25] xylose, [18] isomannide, [19] isosorbide [20][21] and linear sugars [22] among others. Many of these aforementioned carbohydrate based ionic liquids follow the overall same synthetic strategy: First, a for the carbohydrate of choice (e. g. glucose, galactose, ribose, etc.)…”