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  Radical addition of ketones and cyanide to olefins via acid catalyzed formation of intermediate alkenyl peroxides

Shao, W., Lux, M., Breugst, M., & Klussmann, M. (2019). Radical addition of ketones and cyanide to olefins via acid catalyzed formation of intermediate alkenyl peroxides. Organic Chemistry Frontiers, 6(11), 1796-1800. doi:10.1039/C9QO00447E.

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 Creators:
Shao, Wen1, Author           
Lux, Marcel1, Author           
Breugst, Martin2, Author
Klussmann, Martin1, Author           
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              
2Universität zu Köln, Department für Chemie, Greinstraße 4, 50939 Köln, Germany, ou_persistent22              

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 Abstract: A Brønsted acid catalyzed method was developed for the synthesis of γ-cyanoketones from sulfonyl cyanides, olefins and ketones. The reaction is believed to proceed via intermediate formation of alkenyl peroxides by condensation of ketones with tert-butylhydroperoxide. These unstable compounds decompose by homolytic O–O bond cleavage, generating ketone-derived radicals which add to the olefins and generate the final products after reaction with the sulfonyl cyanide, thereby forming two new C–C bonds. A range of different ketones and olefins can be used, including steroidal ketones and simple alkyl olefins. The products can be further transformed to substituted lactones and piperidines, including a tetracyclic one. This reaction can thus be utilized to gain access to complex molecules from simple starting materials in only a few synthetic steps.

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Language(s): eng - English
 Dates: 2019-03-282019-04-172019-04-182019-06-07
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/C9QO00447E
 Degree: -

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Title: Organic Chemistry Frontiers
  Abbreviation : Org. Chem. Front.
Source Genre: Journal
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Publ. Info: London : Royal Society of Chemistry
Pages: - Volume / Issue: 6 (11) Sequence Number: - Start / End Page: 1796 - 1800 Identifier: ISSN: 2052-4129
CoNE: https://pure.mpg.de/cone/journals/resource/2052-4129