Organic Electrode Reactions - Fundamentals and Applications of Organic Electrochemistry - page 160

(5.23)

5.7.3 Benzylic Electrochemical
Fluorination

Although anodic benzylic substitution reactions
take place readily, anodic benzylic fluorination
does not always occur. The major competitive
reaction is acetamidation when MeCN is used
as a solvent. For example, electrochemical
benzylic fluorination in MeCN proceeded
selectively when the p -position of the phenyl
group was substituted by an electron-donating
group, as shown in Eq. 5.24 [75]. In contrast,
α-acetoamidation became the major reaction
when the phenyl group had no

electron-donating substituent.

(5.24)

Mono- and difluorination can be performed
selectively depending on applied potential.