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
Efficient DBU accelerated synthesis of F-18-labelled trifluoroacetamides
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-1333-7740
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-4299-8860
Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
Show others and affiliations
2016 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, no 97, p. 13963-13966Article in journal (Refereed) Published
Abstract [en]

Nucleophilic F-18-fluorination of bromodifluoromethyl derivatives was performed using [F-18] Bu4NF in the presence of DBU(1,8-diazabicyclo[5.4.0]undec-7-ene). This novel procedure provided a diverse set of [F-18] trifluoroacetamides in good to excellent radiochemical conversions. A mechanism where DBU acts as organomediator in this transformation is proposed.

Place, publisher, year, edition, pages
2016. Vol. 52, no 97, p. 13963-13966
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-139349DOI: 10.1039/c6cc08535kISI: 000390436700005PubMedID: 27844069OAI: oai:DiVA.org:su-139349DiVA, id: diva2:1072378
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationAvailable from: 2017-02-07 Created: 2017-02-06 Last updated: 2019-12-16Bibliographically approved
In thesis
1. Development of new Fluorination Methods Directed to Fluorine-18 Labelling
Open this publication in new window or tab >>Development of new Fluorination Methods Directed to Fluorine-18 Labelling
2019 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with the development of new fluorination reactions and their application to fluorine-18 labelling. Fluorine-18 labelled compounds are employed as tracers in Positron Emission Tomography (PET), which is a powerful non-invasive imaging method in medical diagnostics.

The first part of this thesis focuses on the development of a late-stage halogen exchange-based fluorination method for the synthesis of trifluoromethylated molecules. The first project in this area relies on the application of a copper(I)-based fluorinating reagent to furnish trifluoroacetates, trifluorotoluenes and trifluoroacetamides. The second project involves the translation of this methodology into the fluorine-18 labelling of tertiary and secondary trifluoroacetamides. The targeted substrates were labelled in high radiochemical yield and high molar activity using [18F]Bu4NF as fluorine source in the presence of an organic activator.

In the second part, the development of electrophilic fluorination reactions using a hypervalent iodine-based reagent is discussed. The first project in this area addresses the development of an electrophilic fluorine-18 fluorination reagent: [18F]fluoro-benziodoxole. The utility of this reagent was demonstrated in the labelling of [18F]fluoro-benzoxazepines. In the second project, the same [18F]fluoro-benziodoxole reagent was used in the rhodium-mediated synthesis of α-[18F]fluoroethers. High molar activities were obtained in these electrophilic labelling processes. In the third project, the fluorine-19 analog fluoro-benziodoxole was used in the palladium-catalyzed iodofluorination of allyl benzenes, styrenes and cycloalkenes. Both iodine and fluorine atoms in the product arise from the same reagent.

Place, publisher, year, edition, pages
Sockholm: Department of Organic Chemistry, Stockholm University, 2019. p. 73
Keywords
fluorine, fluorine-18, late-stage, labelling, nucleophilic, electrophilic, fluorination, positron emision tomography, PET, hypervalent iodine, benziodoxole, metal-free, DBU, copper, palladium, rhodium, carbene
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-175601 (URN)978-91-7797-919-7 (ISBN)978-91-7797-920-3 (ISBN)
Public defence
2020-01-20, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 15:00 (English)
Opponent
Supervisors
Available from: 2019-12-16 Created: 2019-11-05 Last updated: 2019-11-27Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textPubMed

Search in DiVA

By author/editor
Bermejo Gómez, AntonioCortés González, Miguel A.Lübcke, MarvinSzabó, Kálmán J.
By organisation
Department of Organic Chemistry
In the same journal
Chemical Communications
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
pubmed
urn-nbn

Altmetric score

doi
pubmed
urn-nbn
Total: 55 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