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[F-18]fluoro-benziodoxole: a no-carrier-added electrophilic fluorinating reagent. Rapid, simple radiosynthesis, purification and application for fluorine-18 labelling
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0003-4299-8860
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. AstraZeneca PET Centre at Karolinska Institutet, Sweden.ORCID-id: 0000-0002-1333-7740
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-8834-9834
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Antal upphovsmän: 72018 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 54, nr 34, s. 4286-4289Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Operationally simple radiosynthesis and purification of [F-18]fluoro-benziodoxole was developed starting from a cyclotron produced [F-18]F- precursor, [F-18]TBAF, and tosyl-benziodoxole. The synthetic utility of [F-18]fluoro-benziodoxole was demonstrated by electrophilic fluorocyclization of o-styrilamides proceeding with high RCC (typically 50-90%) and high molar activity (up to 396 GBq mol(-1)).

Ort, förlag, år, upplaga, sidor
2018. Vol. 54, nr 34, s. 4286-4289
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-156663DOI: 10.1039/c8cc00526eISI: 000430935200013PubMedID: 29632936OAI: oai:DiVA.org:su-156663DiVA, id: diva2:1213159
Tillgänglig från: 2018-06-04 Skapad: 2018-06-04 Senast uppdaterad: 2019-12-02Bibliografiskt 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

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Cortés González, Miguel A.Bermejo Gómez, AntonioMeyer, Denise N.Szabó, Kálmán J.
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Institutionen för organisk kemi
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Chemical Communications
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