Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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
Transition metal-catalysed enol formation from allylic alcohols: Isomerisation, C−C and C−F bond formations
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis describes the isomerisation of allylic alcohols into enols and enolates catalysed by transition metal complexes. The transformation has been used to prepare both unsubstituted and α-substituted carbonyl compounds. Significant attention has been given to the mechanistic aspects of the reactions.

In the first part of this thesis, an environmentally benign procedure for the redox isomerisation of allylic alcohols into ketones is described. The reaction takes place in water and at room temperature using a cationic rhodium complex in combination with water-soluble phosphines. A variety of allylic alcohols could be isomerised in high yields using this procedure.

The second part describes the combination of an allylic alcohol isomerisation with a C−C bond formation, catalysed by a rhodium complex. In this way, allylic alcohols were coupled with aldehydes and N-tosyl imines forming aldol and Mannich-type products. In addition, homoallylic and bishomoallylic alcohols were for the first time isomerised into the corresponding enolates and coupled using this methodology.

In the third part of this thesis, the isomerisation of allylic alcohols was coupled with a C−F bond formation using an iridium complex and electrophilic fluorinating reagents. This novel transformation was used to convert allylic alcohols into single regioisomers of α-fluoroketones. The reaction is tolerant to air and water and takes place at room temperature.

All of the reactions described take place under mild conditions, are operationally simple, and utilise catalysts formed in situ from commercially available metal complexes and ligands.

Place, publisher, year, edition, pages
Stockholm University , 2011. , 42 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-58005OAI: oai:DiVA.org:su-58005DiVA: diva2:419415
Presentation
2011-06-17, Magnéli Hall, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 14:00
Opponent
Funder
Knut and Alice Wallenberg Foundation
Available from: 2011-05-26 Created: 2011-05-26 Last updated: 2011-06-28Bibliographically approved

Open Access in DiVA

No full text

Search in DiVA

By author/editor
Ahlsten, Nanna
By organisation
Department of Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric score

urn-nbn
Total: 160 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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