Use of perfluoro groups in nucleophilic 18 F‐fluorination

Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [ 18 F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluor...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2010-01, Vol.53 (1), p.24-30
Main Authors: Blom, Elisabeth, Karimi, Farhad, Långström, Bengt
Format: Article
Language:English
Subjects:
chemical reactivity
Chemistry
F-SPE
Kemi
NATURAL SCIENCES
NATURVETENSKAP
nucleophilic 18F-fluorination
perfluoro
purification
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Summary:Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [ 18 F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18 F‐fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [ 18 F]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.
ISSN:0362-4803
1099-1344
1099-1344
DOI:10.1002/jlcr.1695