Synthetic Transformations Using Molecular Oxygen-Doped Carbon Materials

Carbon materials like activated carbon (AC) undergo chemisorption with O₂ to give species with electron deficiency in the carbon skeleton and negative charge at the oxygen end that upon reaction with PPh₃ and benzoic acid afford Ph₃P═O. Whereas amine donors react with O₂-chemisorbed AC and nucleophiles to give dehydrogenatively coupled products in 67-89% yields via the corresponding radical cation and iminium ion intermediates, the reactions using β-naphthoxide derivatives give the corresponding oxidatively coupled bi-2-naphthol products in 68-95% yields.