Organic Electrode Reactions - Fundamentals and Applications of Organic Electrochemistry - page 122

bond formation and carbon-heteroatom bond
cleavage [5-8].
Figure 5.1 Indirect anodic oxidation of
alcohols using iodine mediator
5.1.2.3 Electrosynthesis Using Triarylamine
Mediators
Triarylamines, which are well known as outer
sphere electron transfer reagents, were first
used as mediators for anodic oxidative
deprotection of a protective group like
dithiolane for a carbonyl group by Steckhan
( Eq. 5.4 ) [2]. The oxidation ability of this
mediator can be tuned by substitution with
electron-withdrawing groups such as the
bromine atom, as shown in Table 5.3 .
Triarylamine mediators can be applied to
oxidation of alcohols, amines and the
side-chain of aromatic compounds, together
with fluorodesulfurization. Thus, they are
highly useful and widely applicable mediators.