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

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

Konstantin Evgen'evich Shepelenko 1, 2
Konstantin Evgen'evich Shepelenko
, 
Maxim Aleksandrovich Shevchenko 2
Maxim Aleksandrovich Shevchenko
, 
Yurii Nikolaevich Tkachenko 2
Yurii Nikolaevich Tkachenko
,  , 
Viktor Mikhailovich Chernyshev 1, 2
Viktor Mikhailovich Chernyshev
10.71267/mencom.7920
Published 2026-02-03
Communication , Volume 36, Issue 2, 177-179
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Shepelenko K. E. et al. Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 177-179.
GOST all authors (up to 50) Copy
Shepelenko K. E., Shevchenko M. A., Tkachenko Y. N., Minyaev M. E., Chernyshev V. M. Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 177-179.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7920
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7920
TI - Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes
T2 - Mendeleev Communications
AU - Shepelenko, Konstantin Evgen'evich
AU - Shevchenko, Maxim Aleksandrovich
AU - Tkachenko, Yurii Nikolaevich
AU - Minyaev, Mikhail Evgenievich
AU - Chernyshev, Viktor Mikhailovich
PY - 2026
DA - 2026/02/03
PB - Mendeleev Communications
SP - 177-179
IS - 2
VL - 36
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2026_Shepelenko,
author = {Konstantin Evgen'evich Shepelenko and Maxim Aleksandrovich Shevchenko and Yurii Nikolaevich Tkachenko and Mikhail Evgenievich Minyaev and Viktor Mikhailovich Chernyshev},
title = {Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7920},
number = {2},
pages = {177--179},
doi = {10.71267/mencom.7920}
}
MLA
Cite this
MLA Copy
Shepelenko, Konstantin Evgen'evich, et al. “Synthesis and transformations of mesoionic imidazol-3-ium-4-olate carbaldehydes.” Mendeleev Communications, vol. 36, no. 2, Feb. 2026, pp. 177-179. https://mendcomm.colab.ws/publications/10.71267/mencom.7920.

Keywords

formylation
imidazol-3-ium-4-olates
ligands
mesoionic compounds
N-heterocyclic carbenes
Vilsmeier--Haack reaction

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.

Funders

Russian Science Foundation
23-73-00088

References

1.
Synthetic Routes to Late Transition Metal–NHC Complexes
Scattolin T., Nolan S.P.
Trends in Chemistry, 2020
2.
Recent advances in the chemistry and applications of N-heterocyclic carbenes
Bellotti P., Koy M., Hopkinson M.N., Glorius F.
Nature Reviews Chemistry, 2021
4.
Design Concepts for N-Heterocyclic Carbene Ligands
Nahra F., Nelson D.J., Nolan S.P.
Trends in Chemistry, 2020
7.
Stabilization of the Pd–NHC framework with 1,2,4-triazol-5-ylidene ligands toward decomposition in alkaline media
Chernenko A.Y., Astakhov A.V., Kutyrev V.V., Gordeev E.G., Burykina J.V., Minyaev M.E., Khrustalev V.N., Chernyshev V.M., Ananikov V.P.
Inorganic Chemistry Frontiers, 2021
8.
Base‐Ionizable Anionic NHC Ligands in Pd‐catalyzed Reactions of Aryl Chlorides
Chernenko A., Baydikova V., Kutyrev V., Astakhov A., Minyaev M., Chernyshev V., Ananikov V.P.
ChemCatChem, 2024
10.
A Hybrid Ring-Opening Metathesis Polymerization Catalyst Based on an Engineered Variant of the β-Barrel Protein FhuA
Philippart F., Arlt M., Gotzen S., Tenne S., Bocola M., Chen H., Zhu L., Schwaneberg U., Okuda J.
Chemistry - A European Journal, 2013
11.
Ruthenium Complex Bearing a Hydroxy Group Functionalised N‐Heterocyclic Carbene Ligand – A Universal Platform for Synthesis of Tagged and Immobilised Catalysts for Olefin Metathesis
Monsigny L., Czarnocki S., Sienkiewicz M., Kopcha W., Frankfurter R., Vogt C., Solodenko W., Kajetanowicz A., Kirschning A., Grela K.
European Journal of Organic Chemistry, 2021
12.
One-Step Access to Heteroatom-Functionalized Imidazol(in)ium Salts.
Pasyukov D.V., Shevchenko M.A., Shepelenko K.E., Khazipov O.V., Burykina J.V., Gordeev E.G., Minyaev M.E., Chernyshev V.M., Ananikov V.P.
Angewandte Chemie - International Edition, 2022
13.
4‐Halomethyl‐Substituted Imidazolium Salts: a Versatile Platform for the Synthesis of Functionalized NHC Precursors
Chernyshev V., Pasyukov D.V., Shevchenko M.A., Minyaev M.E., Ananikov V.P.
Chemistry - An Asian Journal, 2024
14.
Khazipov O.V., Pyatachenko A.S., Khazipova O.V., Chapurny I.A., Pasyukov D.V., Minyaev M.E., Chernyshev V.M.
Mendeleev Communications, 2025
15.
Facile Derivatization of a “Chemo-active” NHC Incorporating an Enolate Backbone and Relevant Tuning of Its Electronic Properties
Benhamou L., Vujkovic N., César V., Gornitzka H., Lugan N., Lavigne G.
Organometallics, 2010
17.
IMes-acac: hybrid combination of diaminocarbene and acetylacetonato sub-units into a new anionic ambidentate NHC ligand
César V., Mallardo V., Nano A., Dahm G., Lugan N., Lavigne G., Bellemin-Laponnaz S.
Chemical Communications, 2015
18.
Homo- and Heteropolymetallic Complexes of the Hybrid, Ambidentate N-Heterocyclic Carbene Ligand IMes-acac
César V., Mallardo V., Nano A., DePeter S.F., Bastin S., Sournia-Saquet A., Maisse-François A., Lugan N., Bellemin-Laponnaz S.
ACS Omega, 2018