Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-8977-4963
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-9085-0476
2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 8, 1779-1783 p.Article in journal (Refereed) Published
Abstract [en]

An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.

Place, publisher, year, edition, pages
2017. Vol. 23, no 8, 1779-1783 p.
Keyword [en]
acyloximes, iron, pyrroles, radicals, silyl enol ethers
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-140136DOI: 10.1002/chem.201605636ISI: 000395754800009OAI: oai:DiVA.org:su-140136DiVA: diva2:1077710
Funder
The Wenner-Gren Foundation
Available from: 2017-02-28 Created: 2017-02-28 Last updated: 2017-05-02Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Yang, Hai-BinSelander, Nicklas
By organisation
Department of Organic Chemistry
In the same journal
Chemistry - A European Journal
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 288 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf