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Synfacts 2014; 10(1): 0078
DOI: 10.1055/s-0033-1340373
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

[18F]Trifluoromethylation of Aryl and Heteroaryl Iodides

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Huiban M, Tredwell M, Mizuta S, Wan Z, Zhang X, Collier TL, Gouverneur V, * Passchier J. * Imperial College London and University of Oxford, UK; GlaxoSmithKline, Shanghai, P. R. of China; Advion BioSystems, Ithaca, USA
A Broadly Applicable [18F]Trifluoromethylation of Aryl Iodides and Heteroaryl Iodides for PET Imaging.

Nature Chem. 2013;
5: 941-944
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

copper - [18F]trifluoromethylation - aryl iodides - heteroaryl iodides

Significance

The authors disclose the easy and broadly applicable late-stage [18F]trifluoromethylation of various aryl and heteroaryl iodides using methyl chlorodifluoroacetate, CuI, TMEDA, and [18F]fluoride. The [18F]trifluoromethylated (hetero)aryls, which serve as [18F]-PET (positron emission tomography) tracers, are obtained in good yields.


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Comment

Usually, access to [18F]-labelled probes is limited by the short half-life of 18F and the small availability of parent 18F sources that show a suitable reactivity, such as [18F]F– and [18F]F2. Furthermore, this operational simple [18F]CuCF3-based strategy excludes the tedious preparation of complex organometallic precursors and may be performed on air. The active [18F]CF3Cu is generated in situ.


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