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Research Article
Use of perfluoro groups in nucleophilic 18F-fluorination
Article first published online: 25 NOV 2009
DOI: 10.1002/jlcr.1695
Copyright © 2009 John Wiley & Sons, Ltd.
Issue
1099-1344/asset/cover.gif?v=1&s=4b6abb1d01cc23d5bd78456a499412dee92e9998 "Journal of Labelled Compounds and Radiopharmaceuticals")
Journal of Labelled Compounds and Radiopharmaceuticals
Volume 53, Issue 1, pages 24–30, January 2010
Additional Information
How to Cite
Blom, E., Karimi, F. and Långström, B. (2010), Use of perfluoro groups in nucleophilic 18F-fluorination. Journal of Labelled Compounds and Radiopharmaceuticals, 53: 24–30. doi: 10.1002/jlcr.1695
Publication History
- Issue published online: 8 JAN 2010
- Article first published online: 25 NOV 2009
- Manuscript Revised: 13 NOV 2009
- Manuscript Accepted: 12 OCT 2009
- Manuscript Received: 8 JUL 2009
- Abstract
- Article
- References
- Cited By
Keywords:
- perfluoro;
- nucleophilic 18F-fluorination;
- F-SPE;
- chemical reactivity;
- purification
Graphical Abstract
Perfluorous structures were applied as a part of a leaving group in labelling chemistry. [18F](Fluoromethyl)benzene was used as the model target compound. Several precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18F-fluorination and the impact on the reactivity of the substitution reaction and its use in the purification by fluorous solid phase extraction (F-SPE) was explored. Copyright © 2009 John Wiley & Sons, Ltd.
Abstract
Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [18F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18F-fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [18F]Fluoride interacted with perfluoroalkyl chains, precluding nucleophilic substitution. When perfluoroaryl groups were used, the substitution proceeded, and the separation of product was explored. The radiolabelled product was obtained in 32% analytical yield and the radiochemical purity was increased to approximately 77% using fluorous solid phase extraction purification. Copyright © 2009 John Wiley & Sons, Ltd.