Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile

Anodic benzylic fluorination of alkylbenzenes was comparatively studied in MeCN using Et₄NF-4HF as a supporting electrolyte and a fluorine source. The anodic benzylic fluorination proceeded except for some cumene derivatives and the yields of fluorinated products greatly depended on the stability of the benzylic cation intermediates. It was found that fluoride ions reacted with more stable benzylic cations preferentially, while acetamidation took place preferentially at less stable benzylic cations.