Organocatalytic, Dioxirane-Mediated C-H Hydroxylation under Mild Conditions Using Oxone

Dioxiranes are among the most selective and useful reagents for C(sp(3)) 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 hydtoxylations 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.