Synthetic Transformations Using Molecular Oxygen-Doped Carbon Materials

Carbon materials like activated carbon (AC) undergo chemisorption with O-2 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 O-2-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 beta-naphthoxide derivatives give the corresponding oxidatively coupled bi-2-naphthol products in 68-95% yields.