A new strategy for the synthesis of imidazolium salts was developed in the joint research of the scientists from the ZIOC and the Platov South-Russian State Polytechnic University

The customizable properties of imidazolium salts and its derivatives, as well as the control of their stability and melting point, have made these compounds extremely popular in many areas of human life. Today, they are considered as promising components of rechargeable batteries, and are also widely used as reaction media and stabilizers of metal nanoparticles. Despite the variety of existing methods for the preparation of imidazolium salts, the synthesis of 4(5)-heteroatom-functionalized derivatives often proceeds as a complex multistage process or has a narrow scope.

As a result of a joint study by the research teams of the Zelinsky and the Platov South-Russian State Polytechnic University under the leadership of Academician V.P. Ananikov, a new strategy for the synthesis of various functionalized imidazolium salts from readily available diazabutadienes was proposed using a simple one-step procedure, scalable to gram amounts. The versatility of the developed approach is ensured by the unique ratio of nucleophilic and electrophilic properties of diazabutadiene compounds, which makes possible their simultaneous cyclocondensation with orthoformate and the introduction of nucleophilic functional groups into the C4(5) position of the imidazole ring. When studying the possible applications of the synthesized structures, it was found that new imidazolium salts are amenable to direct metalation with the formation of metal-N-heterocyclic carbene complexes, which exhibit catalytic activity in the formation of carbon-carbon and carbon-nitrogen bonds.

Source:

Dmitry V. Pasyukov, Maxim A. Shevchenko, Konstantin E. Shepelenko, Oleg V. Khazipov, Julia V. Burykina, Evgeniy G. Gordeev, Mikhail E. Minyaev, Victor M. Chernyshev, Valentine P. Ananikov One-Step Access to Heteroatom-Functionalized Imidazol(in)ium Salts Angew. Chem. Int. Ed., 2022, accepted manuscript. DOI: 10.1002/anie.202116131.