4 years ago

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

Organocatalytic, Dioxirane-Mediated C–H Hydroxylation under Mild Conditions Using Oxone
Michael K. Hilinski, Shea L. Johnson, William G. Shuler
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02178

DOI: 10.1021/acs.orglett.7b02178

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