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- Title
Acid-Catalyzed Oxidative Radical Addition of Ketones to Olefins.
- Authors
Schweitzer‐Chaput, Bertrand; Demaerel, Joachim; Engler, Hauke; Klussmann, Martin
- Abstract
Based on a mechanistic study, we have discovered a Brønsted acid catalyzed formation of ketone radicals. This is believed to proceed via thermally labile alkenyl peroxides formed in situ from ketones and hydroperoxides. The discovery could be utilized to develop a multicomponent radical addition of unactivated ketones and tert-butyl hydroperoxide to olefins. The resulting γ-peroxyketones are synthetically useful intermediates that can be further transformed into 1,4-diketones, homoaldol products, and alkyl ketones. A one-pot reaction yielding a pharmaceutically active pyrrole is also described.
- Subjects
ACID catalysts; KETONES; OXIDATIVE addition; ALKENES; BRONSTED acids; HYDROPEROXIDES
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 33, p8737
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201401062