Oxidation and reduction of phenols

Formation of Strecker Aldehydes from Polyphenol-Derived Quinones and α-Amino Acids in a Nonenzymic Model System

“…We envisioned an analogous nonenzymic system in which iron (III) in inorganic ferricyanide Fe(CN) 6 -3 ion could substitute for enzymic copper ions to act as a sink for electrons from catechol reactants. The use of ferricyanide salts for oxidation for phenols is well-known (10), and for monohydric phenols, electron transfer from phenolate (ArO -) is known to form phenoxy radicals (ArO•). Reasoning by analogy, we predicted that the reaction of a catechol with 2 equiv of ferricyanide in a buffer suitable to provide catechol ionization would generate a diradical (•O-Ar-O•) that could then isomerize to a o-quinone.…”

Synthesis of substituted 2,2'- and 4,4'-biphenyldiols using oxidative coupling reaction

“…Известно также, что FeCl3•6H2O и K3[Fe(CN)6] являются эффективными, дешевыми и широко используемыми реагентами для окислительной димеризации фенолов [8][9][10]. Использование данных одноэлектронных окислителей часто позволяет достичь высоких выходов целевых продуктов и может быть пригодно для крупнотоннажного синтеза [11,12].…”

Synthesis of substituted 2,2'- and 4,4'-biphenyldiols using oxidative coupling reaction

“…FeCl3•6H2O and K3[Fe(CN)6] are also known to be efficient, cheap, and widely used reagents for the oxidative dimerisation of phenols [8][9][10]. The use of these one-electron oxidants often provides high yields of target products, and may be suitable for large tonnage synthesis [11,12].…”