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Journal Article

Synergistic Effect of Ketone and Hydroperoxide in Brønsted Acid Catalyzed Oxidative Coupling Reactions

MPS-Authors
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Schweitzer-Chaput,  Bertrand
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Sud,  Abhishek
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Pintér,  Áron
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Dehn,  Stefanie
Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schulze,  Philipp
Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Klussmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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anie_201306752_sm_miscellaneous_information.pdf
(Supplementary material), 2MB

Citation

Schweitzer-Chaput, B., Sud, A., Pintér, Á., Dehn, S., Schulze, P., & Klussmann, M. (2013). Synergistic Effect of Ketone and Hydroperoxide in Brønsted Acid Catalyzed Oxidative Coupling Reactions. Angewandte Chemie International Edition, 52(50), 13228-13232. doi:10.1002/anie.201306752.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-C8FE-B
Abstract
Waste not wasted: A mechanistic study of the autoxidative coupling of xanthene with cyclopentanone uncovered an autoinductive effect of the waste product hydrogen peroxide. It generates radicals in the presence of acid and ketones, which accelerate the reaction by providing an additional pathway to the reactive hydroperoxide intermediate. This discovery could be applied to achieve other Brønsted acid-catalyzed oxidative coupling reactions.