Benzimidazolium salts bearing 4-florobenzyl group: Synthesis and characterization

5th International Organic Chemistry Congress, Malatya, Türkiye, 14 - 17 Ekim 2021, ss.37

N-heterocyclic carbenes (NHCs) that were published independently by Wanzlick and Öfele in 1968 were known as unstable

intermediates at the quarter of a century [1]. In the NHC ligands, both the σ electron-attracting and π electron-donating

character of the carbene center and the nitrogen centers impart electron-rich nucleophilic properties to the NHC ligand [2].

The fluorine atom is the most electronegative element in the periodic table. The presence of fluorine atoms in a compound

affects the structure, reactivity, and functionality of the compound. Numerous hydrofluorocarbon compounds are used in

pharmaceuticals, materials, polymers, refrigeration, air-conditioning, agrochemicals, and photovoltaic solar cells.

Furthermore, functionalizing a molecule with fluorine atoms or a fluorinated group is a common strategy used in the

pharmaceutical field to modulate the metabolism, lipophilicity, acidity, structure, and even metabolism of a given drug. Thanks

to this strategy, around 200 fluorine-containing drugs are produced on the market, as well as new drugs, some of which are

best-selling drugs [3-5]. In our study, we have reported the synthesis of the 4-florobenzyl-substituted benzimidazolium salts 1a-d. The salts were

prepared from the 1-alkylbenzimidazole and 4-florobenzyl bromide. The benzimidazolium salts have been characterized by

using 1H NMR, 13C NMR, FTIR spectroscopy, and elemental analysis techniques.