This electrooxidative protocol cleaves C-C bonds in polycyclic aromatic hydrocarbons, indicating broad applicability.
Cleavage of aromatic C-C bonds remains a formidable challenge in organic synthesis due to their exceptional stability. We describe an electrooxidative protocol that enables selective cleavage of peripheral C-C bonds in various polycyclic aromatic hydrocarbons (PAHs) under anodic oxidation conditions in DMF, affording dicarbonyl products. In addition to phenacenes, this method cleaves the peripheral bond of corannulene and the inner bond of dibenzo[g,p]chrysene, demonstrating a broad applicability for PAH bond activation.
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Sakamoto et al. (2025) studied this question.
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