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 H(2)O have been developed. With ß-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, ß-cyclodextrin selectively enhanced the C-H bond oxidation of cumene in a mixture of cumene and ethyl benzene in H(2)O. Through (1)H NMR studies, the selectivity in C-H bond oxidation could be attributed to the inclusion complex formation between ß-cyclodextrin and the substrates.