(Digital Presentation) Electrocatalytic Transformations of Phenolic Compounds

Abstract

Electrocatalytic transformations giving rise to new C-C bond formation and new products are of value. We have recently discovered that phenolic compounds undergo selective electrochemical oxidation giving rise to reactive radicals which combine to produce product with new C-C bond formed [1]. A series of phenolic compounds, including butylated hydroxytoluene (BHT), 4-tert-butylphenol (4TBP), 2-tert-butylphenol (2TBP), 2,4,6-tri-tert-butylphenol (TTBP), 2,6,-di-tert-butylphenol (DTBP), diphenylphenol (DPP), and trichlosan were systematically evaluated by electrochemical methods.The selective electrochromic behavior was observed via electrochemical cycling. The electrocatalytic oxidation of substrates resulted in a formation of new compounds due to C-C coupling, or related products. The products were characterized by X-ray diffraction, GC-MS, and NMR, among other methods. The electrochemical synthesis was compared to the traditional chemical synthesis and the reaction yields and products were highly dependent on the synthetic strategy used and a substrate. References Zabik, N., Virca, C. N., McCormick, T., Martic-Milne, S. (2016). Selective electrochemical versus chemical oxidation of bulky phenols. J. Phys. Chem. B. 120: 8914-8924.