Selective and one-pot formation of phenols by anodic oxidation

✍ Scribed by Kazuo Fujimoto; Yuichiro Tokuda; Hirofumi Maekawa; Yoshiharu Matsubara; Takumi Mizuno; Ikuzo Nishiguchi

• Book ID: 104207309
• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 367 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)00056-7

✦ Synopsis

Direct monohydroxylation of benzene and substituted benzenes was successfully performed by anodic oxidation to form the corresponding phenol derivatives in good yields. The anodic oxidation was generally carded out in a mixed solvent of trifluoroacetic acid and dichloromethane containing triethylamine using a divided cell equipped with a platinum plate as the anode, a carbon rod as the cathode. Benzene derivatives having electron withdrawing groups were suitable for the present electrochemical oxidation. It was clarified that aryltrifluoroacetates were formed as the initial products from the reaction of the radical cations, generated by one electron transfer from the substrates, with trifluoroacetic acid, followed by hydrolysis during work-up to give the corresponding phenols.