An efficient approach to phenols and aldehydes through the formation of hydroperoxides from alkylbenzenes was successfully achieved by aerobic oxidation using N-hydroxyphthalimide (NHPI) as a catalyst. The oxidation of various alkyl, benzenes with dioxygen by NHPI followed by treatment with a Lewis acid or triphenylphosphine led to phenols or aldehydes, respectively, in good yields. For example, the aerobic oxidation of cumene in the presence of a catalytic amount of NHPI at 75degreesC and subsequent treatment with H2SO4 gave phenol in 77% yield. 1,4-Dihydroxybenzene (61%) and 4-isopropylphenol (33%) were obtained from 1,4-disopropylbenzene. On the other hand, dibenzyl ether was converted into phenol or benzaldehyde upon treatment of the resulting hydroperoxide with InCl3 or PPh3, respectively.
Photolactonisierung: Ein neuer synthetischer Zugang zu Makroliden