Oxidation of α-trifluoromethyl and non-fluorinated alcohols the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good y...

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Published in:Organic & biomolecular chemistry 2018-06, Vol.16 (25), p.4715-4719
Main Authors: Pistritto, Vincent A, Paolillo, Joshua M, Bisset, Kathryn A, Leadbeater, Nicholas E
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Summary:We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields. The merger of oxoammonium cation mediated oxidation with visible-light photoredox catalysis is demonstrated in the oxidation of α-trifluoromethyl and non-fluorinated alcohols.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01063c