Carboxylation of styrenes under constant voltage
in the presence of ammonium salts
Nurlan Turmagambetov
Department of Chemistry, School of Science and Humanities,
Nazarbayev University, Nur-Sultan, Kazakhstan
Email: [email protected]
Abstract
Carboxylation of double bonds in styrenes under electric current was underdeveloped field of synthetic
chemistry, which attracted a certain degree of attention recently. It was partially due to specificity of the
reaction and its potential use, while also including electrode-inefficient reactions, where the latter were
consumed over the course of the process. It was found possible to use inert carbon electrodes with the aid
of ammonium salts acting as catalysts, which allowed efficient carboxylation to occur with yields up to
about 80%. A series of reactions were performed in order to study the reaction with tetraethylammonium
iodide and quinidine being used as ammonium salts each separately and in equimolar mixture. Three
substrates were carboxylated resulting in total of nine major syntheses being tested. For each reaction, the
products were accessed using both spectral analysis and column chromatography revealing
tetraethylammonium iodide to be rather efficient compared to quinidine by a large margin. Nevertheless,
quinidine has shown the ability to catalyze the reaction and leaves a room for further investigation of
complex ammonium salts as catalysts for such type of reactions.
References:
1. G. Kobra, et al.., Abbas A. J., C. R. Chim., 1 (2018) 14
2. N. Kise, et al.., Ueda N., J. Org. Chem., 7 (2002) 8305
3. S.C. Wang, et al.., Tantillo D. J., J. Org. Chem., 74 (2009) 7822