Organocatalytic, Dioxirane-Mediated C-H Hydroxylation under Mild Conditions Using Oxone
William G Shuler1, Shea L Johnson1, Michael K Hilinski1
1Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
Abstract:
Dioxiranes are among the most selective and useful reagents for C(sp3)-H hydroxylation, but the development of a general dioxirane-mediated catalytic method has been an elusive goal. A trifluoromethyl ketone catalyst in combination with Oxone is shown to enable the first dioxirane-mediated catalytic hydroxylations that approximate the reactivity and selectivity of isolated dioxiranes. The mild reaction conditions allow for selective 3° hydroxylation and 2° oxidation and are tolerant of acid-sensitive functionality and electron-neutral arenes.
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