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Journal Article

An Unexpected α‐Oxidation of Cyclic Ketones with 1,4‐Benzoquinone by Enol Catalysis

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Shevchenko,  Grigory A.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Oppelaar,  Barry
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Shevchenko, G. A., Oppelaar, B., & List, B. (2018). An Unexpected α‐Oxidation of Cyclic Ketones with 1,4‐Benzoquinone by Enol Catalysis. Angewandte Chemie International Edition, 57(33), 10756-10759. doi:10.1002/anie.201804445.


Cite as: http://hdl.handle.net/21.11116/0000-0002-15FA-D
Abstract
The first direct and asymmetric α‐aryloxylation of cyclic ketones via enol catalysis has been achieved using quinones as the reaction partners. Catalytic amounts of a phosphoric acid promote the exclusive formation of α,α‐disubstituted ketones from the corresponding α‐substituted ketones in good yields and enantioselectivities (up to 96.5:3.5 er). Preliminary mechanistic experiments suggest that this reaction proceeds via a proton‐coupled electron transfer (PCET) followed by radical recombination.