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Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination
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 Intitutet, Sweden.
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Number of Authors: 62017 (English)In: Journal of fluorine chemistry, ISSN 0022-1139, E-ISSN 1873-3328, Vol. 194, p. 51-57Article in journal (Refereed) Published
Abstract [en]

The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)(3)CuF is described. Under the reaction conditions, different trifluoroacetates, trifluorolcetones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

Place, publisher, year, edition, pages
2017. Vol. 194, p. 51-57
Keywords [en]
Nucleophilic fluorination, Copper, Trifluoroacetate, Trifluoromethylarene, Trifluoroacetamide
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-141365DOI: 10.1016/j.jfluchem.2016.12.017ISI: 000393938200007OAI: oai:DiVA.org:su-141365DiVA, id: diva2:1092304
Available from: 2017-05-02 Created: 2017-05-02 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)
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Available from: 2019-12-16 Created: 2019-11-05 Last updated: 2019-11-27Bibliographically approved

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Bermejo Gómez, AntonioCortés González, Miguel A.Lübcke, MarvinSzabó, Kálmán J.
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