Aerobic Selective Oxidation of Cyclohexylbenzene Over Organocatalysis with Pairs of Nitrogenous Hydroxyl Precursors and Anthraquinones

Selective oxidation of cyclohexylbenzene is a potentially promising process in industrial application. Herein, we reported an organocatalytic system to achieve the selective oxidation of C α –H bonds in cyclohexylbenzene and transformation of active intermediate C α peroxide by an oxidation then decomposition method. The pair of N -hydroxyphthalimide and 2-Chlorothraquinone (NHPI/AQ-Cl) as metal-free organic catalysts showed the highest efficient in selective oxidation of cyclohexylbenzene to C α peroxide and C α alcohol. And the base modified covalent triazine frameworks could facilitate the C α peroxide decomposition to the C α alcohol. Up to 8.8% conversion of substrate and 80% selectivity of 1-phenylcyoclohexanol were achieved under the optimized conditions. This work provided a new organocatalytic strategy to achieve the aerobic selective oxidation of C α –H bonds in cyclohexylbenzene. Graphical Abstract