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Efficient DBU accelerated synthesis of F-18-labelled trifluoroacetamides
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-1333-7740
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0003-4299-8860
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Karolinska Institutet, Sweden.
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2016 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, nr 97, s. 13963-13966Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
2016. Vol. 52, nr 97, s. 13963-13966
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-139349DOI: 10.1039/c6cc08535kISI: 000390436700005PubMedID: 27844069OAI: oai:DiVA.org:su-139349DiVA, id: diva2:1072378
Forskningsfinansiär
VetenskapsrådetKnut och Alice Wallenbergs StiftelseTillgänglig från: 2017-02-07 Skapad: 2017-02-06 Senast uppdaterad: 2019-12-16Bibliografiskt 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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Bermejo Gómez, AntonioCortés González, Miguel A.Lübcke, MarvinSzabó, Kálmán J.
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Chemical Communications
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