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 ß-naphthoxide derivatives give the corresponding oxidatively coupled bi-2-naphthol products in 68-95% yields.