Selective oxidation of unactivated C–H bonds by supramolecular control

Abstract

Efficient methods for dioxirane-based selective C–H bond oxidation by supramolecular control in H₂O have been developed. With β-cyclodextrin as the supramolecular host, site-selective oxidation of the terminal over the internal tertiary C–H bond of 3,7-dimethyloctyl esters 3a–c was achieved. In addition, β-cyclodextrin selectively enhanced the C–H bond oxidation of cumene in a mixture of cumene and ethyl benzene in H₂O. Through ¹H NMR studies, the selectivity in C–H bond oxidation could be attributed to the inclusion complex formation between β-cyclodextrin and the substrates.