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