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Issue 15, 2020
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Rhenium(i) complexation–dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers

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Abstract

A novel fluorine-18 method employing rhenium(I) mediation is described herein. The method was found to afford moderate to high radiochemical yields of labelled rhenium(I) complexes. Subsequent thermal dissociation of the complexes enabled the radiosynthesis of fluorine-18 labelled pyridine bidentate structures which could not be radiofluorinated hitherto. This rhenium(I) complexation–dissociation strategy was further applied to the radiosynthesis of [18F]CABS13, an Alzheimer's disease imaging agent, alongside other 2,2′-bipyridine, 1,10-phenanthroline and 8-hydroxyquinoline labelled radiotracers. Computational modelling of the reaction mechanism suggests that the efficiency of rhenium(I) activation may be attributed to both an electron withdrawal effect by the metal center and the formation of an acyl fluoride intermediate which anchors the fluoride subsequent to nucleophilic addition.

Graphical abstract: Rhenium(i) complexation–dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers

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Supplementary files

Article information


Submitted
11 Jan 2020
Accepted
10 Feb 2020
First published
28 Feb 2020

This article is Open Access

RSC Adv., 2020,10, 8853-8865
Article type
Paper

Rhenium(I) complexation–dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers

M. A. Klenner, B. Zhang, G. Ciancaleoni, J. K. Howard, H. E. Maynard-Casely, J. K. Clegg, M. Massi, B. H. Fraser and G. Pascali, RSC Adv., 2020, 10, 8853
DOI: 10.1039/D0RA00318B

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