Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Rhodium-mediated 18F-oxyfluorination ofdiazoketones using a fluorine-18-containing hypervalent iodine reagent
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0003-4299-8860
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Visa övriga samt affilieringar
2019 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 55, nr 89, s. 13358-13361Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Geminal 18F-oxyfluorination of diazoketones was performed in the presence of rhodium mediators. The reactions were performed using a hypervalent iodine-based [18F]fluoro-benziodoxole reagent. By this methodology various α-[18F]fluoro ethers were obtained in high radiochemical yield (up to 98%) and molar activity (216 GBq μmol-1).

Ort, förlag, år, upplaga, sidor
2019. Vol. 55, nr 89, s. 13358-13361
Nyckelord [en]
fluorine-18, electrophilic, hypervalent iodine, PET, rhodium, diazo compound
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-175600DOI: 10.1039/c9cc06905dISI: 000496175900002OAI: oai:DiVA.org:su-175600DiVA, id: diva2:1368010
Forskningsfinansiär
VetenskapsrådetKnut och Alice Wallenbergs Stiftelse, 2018.0066Tillgänglig från: 2019-11-05 Skapad: 2019-11-05 Senast uppdaterad: 2019-12-09Bibliografiskt granskad
Ingår i avhandling
1. Development of new Fluorination Methods Directed to Fluorine-18 Labelling
Öppna denna publikation i ny flik eller fönster >>Development of new Fluorination Methods Directed to Fluorine-18 Labelling
2019 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Sockholm: Department of Organic Chemistry, Stockholm University, 2019. s. 73
Nyckelord
fluorine, fluorine-18, late-stage, labelling, nucleophilic, electrophilic, fluorination, positron emision tomography, PET, hypervalent iodine, benziodoxole, metal-free, DBU, copper, palladium, rhodium, carbene
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-175601 (URN)978-91-7797-919-7 (ISBN)978-91-7797-920-3 (ISBN)
Disputation
2020-01-20, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 15:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2019-12-16 Skapad: 2019-11-05 Senast uppdaterad: 2019-11-27Bibliografiskt granskad

Open Access i DiVA

Fulltext saknas i DiVA

Övriga länkar

Förlagets fulltext

Sök vidare i DiVA

Av författaren/redaktören
Cortés González, Miguel A.Jian, XingguoSzabó, Kálmán J.
Av organisationen
Institutionen för organisk kemi
I samma tidskrift
Chemical Communications
Organisk kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 4 träffar
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf