Selective oxidation of unactivated C–H bonds by supramolecular control?

Organic & Biomolecular Chemistry Pub Date: 2012-02-22 DOI: 10.1039/C2OB07069C

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.

Graphical abstract: Selective oxidation of unactivated C–H bonds by supramolecular control
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