Journal
ORGANIC LETTERS
Volume 19, Issue 18, Pages 4790-4793Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02178
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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.
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