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  Acid-Catalyzed Oxidative Radical Addition of Ketones to Olefins

Schweitzer-Chaput, B., Demaerel, J., Engler, H., & Klussmann, M. (2014). Acid-Catalyzed Oxidative Radical Addition of Ketones to Olefins. Angewandte Chemie, International Edition, 53(33), 8737-8740. doi:10.1002/anie.201401062.

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 Creators:
Schweitzer-Chaput, Bertrand1, Author              
Demaerel, Joachim1, Author
Engler, Hauke1, Author
Klussmann, Martin1, Author              
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              

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Free keywords: POLARITY-REVERSAL CATALYST; N-HYDROXYPHTHALIMIDE NHPI; CARBON-CENTERED RADICALS; METAL SALT; CARBONYLATION-PEROXIDATION; MANGANESE(III) ACETATE; PHOTOREDOX CATALYSIS; COUPLING REACTIONS; ORGANIC-SYNTHESIS; ALKENES
 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.

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Language(s): eng - English
 Dates: 2014-04-282014-08-11
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201401062
 Degree: -

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Title: Angewandte Chemie, International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed
  Other : Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed
Source Genre: Journal
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Publ. Info: Weinheim, Deutschland : Wiley-VCH
Pages: - Volume / Issue: 53 (33) Sequence Number: - Start / End Page: 8737 - 8740 Identifier: CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851