Electrochemical Versus Chemical Transformations of Phenolic Compounds

The electrochemical synthesis offers advantages over traditional organic synthesis, due to its milder, greener and more sustainable nature [1]. The reactivity of reagents can be selectively tuned by using various electrode materials, electrolytes, and applied potentials. The irreversible electrooxidation of phenols is a viable route towards new phenol-based and value-added products. Often, the oxidation of phenols leads to quinone production, however, other reactivities such as polymerization and carbon-carbon bond formation are also possible. We have previously reported on the selective carbon-carbon dimerization of bulky phenols via electrochemical synthesis [2]. The electrooxidation was further explored towards dimerization of substituted phenols with extended conjugation. The formation of a dimer was highly dependent on the electrode material, and potential applied. The electrosynthesis was compared to traditional synthesis for chlorinated phenol as well [3]. The reactions were monitored and products characterized by UV-Vis spectroscopy, GC-MS and X-ray diffraction. Current efforts in expanding the electrosynthesis to include a diverse substrate scope will also be described. References Möhle S., Zirbes M, Rodrigo E., Gieshoff T., Wiebe A., Waldvogel S.R. Modern electrochemical aspects for the synthesis of value-added organic products. Chem. 2018 , 57, 6018-6041. Zabik N.L., Virca C.N., McCormick T.M., Martic-Milne S. Selective electrochemical versus chemical oxidation of bulky phenols. Phys. Chem. B. , 2016 , 120, 8914-8924. Lewis T., Gao S., Haas D., Martic S. Electrochemical conversion of triclosan as a greener alternative to chemical oxidation. Electrocatal . 2024 , 15, 474-484.