Indirect Electrochemical Processes. 14. Indirect Electrochemical Oxidation of Benzylic Alcohols with Organic Mediators.

o-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator

“…For example, they are used as a mediator for oxidation reaction of benzyl alcohols to provide benzaldehydes. 7 To study the mediatory behavior of carborane 1, the CV measurements of 1 in the absence and presence of 4-methoxybenzyl alcohol (E p ox = 1.60 V vs. SCE) and 2,6-lutidine were carried out in TBAP/ Scheme 1. DMF at a scan rate of 100 mV/s (Fig.…”

“…As for oxidative mediators, triarylamine derivatives are wellknown and thus utilized for various reactions such as anodic oxidation of benzyl alcohol, 7 anodic deprotection of dithioacetals, 8 and anodic fluorination. 9 A remarkable feature of triarylamines is that the oxidation power can be tuned by molecular design, namely introduction of various substitutents into the aryl moiety.…”

Kinetics of redox mediator tris(4-bromophenyl)amine in acetonitrile and ionic liquid [BMIm][PF6]: Oxidation of benzyl and cyclohexyl alcohols

“…This indicates that the nature of the electrochemical process of TBPA is not significantly changed in RTILs as many compounds have shown a similarity in electrochemical behaviour in conventional organic solvents and in RTILs [17,18]. BA showed a two-electron irreversible oxidation peak corresponding to the formation of aldehyde [8] 6 ], respectively (Fig. 3b).…”

“…The electrochemical behaviour of TBPA in various organic solvents is well known [8,16]. CV of TBPA in acetonitrile containing 0.1 M Et 4 NClO 4 exhibits a well-defined one-electron reversible redox couple at E 1/2 = 0.74 V corresponding to TBPA/TBPA Å+ couple (Fig.…”

“…In this respect, the electrogenerated psubstituted triphenylamine radical-cation is a versatile candidate for the catalytic oxidation of alcohols [7,8], side-chain oxidation of alkyl aromatic compounds [9] and benzylic ethers [10]. The stability of the radical-cation, which in turn determines the reactivity towards the oxidation of a substrate of interest in the medium, markedly depends on the nature of peripheral substituents.…”