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Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes

Frost, Aileen B., Brambilla, Marta, Exner, Rudiger and Tredwell, Matthew 2019. Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes. Angewandte Chemie 131 (2) , pp. 482-486. 10.1002/ange.201810413

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Abstract

A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) of 1 GBq μmol−1. The transformations are operationally simple to perform and were readily translated onto a commercial automated synthesis unit. The resultant 1,1‐[18F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine‐18. 18F‐fluorinated alkenes are excellent building blocks and participate in a number of post‐labeling transformations to access a range of 18F‐perfluorinated functional groups that have never before been radiolabeled with non‐carrier‐added [18F]fluoride. This method considerably expands the range of 18F‐motifs accessible to radiochemists.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Publisher: Wiley-VCH Verlag
ISSN: 0044-8249
Date of Acceptance: 5 October 2018
Last Modified: 05 Jun 2019 10:00
URI: http://orca.cf.ac.uk/id/eprint/122204

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