Communications

Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes

K. E. Shepelenko^ab, M. A. Shevchenko^b, Yu. N. Tkachenko^b, M. E. Minyaev^c, V. M. Chernyshev<sup>ab

a</sup> Skolkovo Institute of Science and Technology, 121205 Moscow, Russian Federation
^b Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
^c N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

Abstract: A simple synthesis of previously inaccessible 1,3-diaryl-5-formyl-1H-imidazol-3-ium-4-olates has been developed via the Vilsmeier–Haack formylation of 4-hydroxy-1,3-diarylimidazolium chlorides. The potential applicability of the obtained 5-formyl-functionalized imidazolium olates to serve as building blocks for preparing diverse multifunctional imidazole compounds has been demonstrated through the reactions with N- and C-nucleophiles.

Keywords: imidazol-3-ium-4-olates, formylation, Vilsmeier–Haack reaction, ligands, N-heterocyclic carbenes, mesoionic compounds.

Received: 18.09.2025
Accepted: 29.10.2025

Language: English

DOI: 10.71267/mencom.7920