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  Synthesis of Oxindoles by Brønsted Acid Catalyzed Radical Cascade Addition of Ketones

Boess, E., Karanestora, S., Bosnidou, A.-E., Schweitzer-Chaput, B., Hasenbeck, M., & Klussmann, M. (2015). Synthesis of Oxindoles by Brønsted Acid Catalyzed Radical Cascade Addition of Ketones. Synlett, 26(14), 1973-1976. doi:10.1055/s-0034-1381052.

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 Creators:
Boess, Esther1, Author              
Karanestora, Sofia2, Author
Bosnidou, Alexandra-Eleni2, Author
Schweitzer-Chaput, Bertrand1, Author              
Hasenbeck, Max2, Author
Klussmann, Martin1, Author              
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              
2external, ou_persistent22              

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Free keywords: ACTIVATED ALKENES; 1,3-DICARBONYL COMPOUNDS; N-ARYLACRYLAMIDES; BOND FORMATION; CARBOCYCLIZATION; SPIROOXINDOLES; ACRYLAMIDES; 1,2-ALKYLARYLATION; FUNCTIONALIZATION; DERIVATIVESChemistry; BrOnsted acid catalysis; radicals; cyclization; heterocycles; peroxides;
 Abstract: Oxindoles bearing ketone side chains in the 3-position can be synthesized by BrOnsted acid catalysis from N-aryl methacrylamides, ketones, and hydroperoxides. The cyclized products are presumably formed in a radical cascade reaction, initiated by decay of intermediate alkenyl peroxides. In the case of acrylic substrates that do not undergo cyclization, -peroxyketones were isolated instead, indicating that the final cyclization step of the cascade does not take place in these cases.

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Language(s): eng - English
 Dates: 2015
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000359998200008
DOI: 10.1055/s-0034-1381052
 Degree: -

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Title: Synlett
  Other : Synlett
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 26 (14) Sequence Number: - Start / End Page: 1973 - 1976 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856