Wednesday, October 23, 2013

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

by Bertrand Schweitzer-Chaput, Abhishek Sud, Áron Pintér, Stefanie Dehn, Philipp Schulze, Martin Klussmann*




Thumbnail image of graphical 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.

Angewandte Chemie International Edition
Article first published online: 22 OCT 2013

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