Radiochemical Synthesis of Alkyl Geminal <sup>18</sup>F-Difluoroalkyl Motifs Mediated by Silver(I) Oxide

<sup>18</sup>F radiotracers are used in positron emission tomography imaging for medical diagnosis and drug development. Current methods to synthesize <sup>18</sup>F-polyfluorinated functional groups are limited in substrate scope and result in radiotracers with low molar activities (<i>A</i><sub><i>m</i></sub>). We disclose the synthesis of a range of <sup>18</sup>F-difluoroalkyl groups by nucleophilic substitution of geminal bromofluoroalkyl electrophiles with [<sup>18</sup>F]fluoride mediated by Ag<sub>2</sub>O. The utility of this transformation to support (pre)clinical imaging is demonstrated by translation to an automated synthesizer.

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Publication Details

Journal
Organic Letters
Published
2025-02-06
DOI
https://doi.org/10.1021/acs.orglett.5c00187
Citations
6
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
4.74

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article

Radiochemical Synthesis of Alkyl Geminal 18F-Difluoroalkyl Motifs Mediated by Silver(I) Oxide

Jasmine Hind, Pawan K. Mishra, Matthew Tredwell, Ian A. Fallis
6 citations
Organic Letters
Fluorine in Organic Chemistry
4.74
article

Radiochemical Synthesis of Alkyl Geminal 18F-Difluoroalkyl Motifs Mediated by Silver(I) Oxide

Jasmine Hind, Pawan K. Mishra, Matthew Tredwell, Ian A. Fallis
article en
6 citations

Abstract

<sup>18</sup>F radiotracers are used in positron emission tomography imaging for medical diagnosis and drug development. Current methods to synthesize <sup>18</sup>F-polyfluorinated functional groups are limited in substrate scope and result in radiotracers with low molar activities (<i>A</i><sub><i>m</i></sub>). We disclose the synthesis of a range of <sup>18</sup>F-difluoroalkyl groups by nucleophilic substitution of geminal bromofluoroalkyl electrophiles with [<sup>18</sup>F]fluoride mediated by Ag<sub>2</sub>O. The utility of this transformation to support (pre)clinical imaging is demonstrated by translation to an automated synthesizer.

Organic LettersVol. 27(7)
University Hospital of Wales (GB), Cardiff University (GB)
Engineering and Physical Sciences Research Council
Good health and well-being
Openalex Percentile: Top 6%
Fluorine in Organic Chemistry
4.74
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