Evolution of the Reagent for Iodination and Iodonitration. Optimization of the Synthesis Conditions in the Framework of Green Chemistry

• Published in: Journal of Siberian Federal University. Chemistry 2023-01, Vol.16 (1), p.145-153
• Main Authors: Tveryakova, Elena N, Perederina, Irina A, Miroshnichenkoa, Yuliya Yu, Golubina, Olga A, Yusubov, Mekhman S, Zykova, Mariya V
• Format: Article
• Language: Russian
• Subjects: Chemical properties; Chemical synthesis; Evolution; Iodination; Iodine; Nitrates; Nitration; Optimization; Potassium iodides; Reagents; Solid phases; Solvents; Substrates
• ISSN: 1998-2836; 2313-6049

The evolution of the Tronov-Novikov reagent is shown. Scientific investigations of our research group under the leading of professor M. S. Usubov in the field of iodination and iodonitration have been analyzed. New possibilities of a solid-phase reagent based on iodine (potassium iodide) and (or) nitrates are represented. We have studied chemical properties of the solid-phase reagents and optimized conditions of reactions, which allow prediction the synthesis of products of mono- or diiodination, iodonitration, nitration, and heterocyclization. It has been found that iodination of activated and mild activated aromatic substrates and phenylacetylene under solvent-free conditions results with products similar to those obtained in the presence of solvent. However, the solvent-free procedure offers significant advantages such as higher yields, short reaction times with mild reaction conditions. Possible redox schemes were proposed for the formation of potential intermediate particles diiodosilver(I) nitrate and nitrile iodide in solvent-free reactions. Obtained theoretical and experimental data confirm the possibility of the homo- and heterolytic pathways decomposition of nitrile iodide, depending on the nature of the substrate, in the synthesis with a solvent, as well as under "solvent-free" conditions.