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Synthesis 2019; 51(23): 4401-4407
DOI: 10.1055/s-0039-1690012
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of [18F]-γ-Fluoro-α,β-unsaturated Esters and Ketones via Vinylogous 18F-Fluorination of α-Diazoacetates with [18F]AgF

Stephen Thompson 
a   Department of Radiology, University of Michigan Medical School, Ann Arbor, MI 48109, USA   Email: pjhscott@umich.edu
,
So Jeong Lee
a   Department of Radiology, University of Michigan Medical School, Ann Arbor, MI 48109, USA   Email: pjhscott@umich.edu
,
Isaac M. Jackson
a   Department of Radiology, University of Michigan Medical School, Ann Arbor, MI 48109, USA   Email: pjhscott@umich.edu
,
Naoko Ichiishi
b   Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA   Email: mssanfor@umich.edu
,
Allen F. Brooks
a   Department of Radiology, University of Michigan Medical School, Ann Arbor, MI 48109, USA   Email: pjhscott@umich.edu
,
Melanie S. Sanford  ∗
b   Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA   Email: mssanfor@umich.edu
,
Peter J. H. Scott  ∗
a   Department of Radiology, University of Michigan Medical School, Ann Arbor, MI 48109, USA   Email: pjhscott@umich.edu
› Author AffiliationsWe acknowledge U.S. Department of Energy/National Institute of Biomedical Imaging and Bioengineering (NIBIB) (DE-SC0012484 to P.J.H.S.) and National Institutes of Health (R01EB021155 to M.S.S. and P.J.H.S.) for financial support.
Further Information

Publication History

Received: 01 July 2019

Accepted after revision: 16 July 2019

Publication Date:
30 July 2019 (online)

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Published as part of the Special Topic Halogenation methods (with a view towards radioimaging applications)

Abstract

This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate [18F]-γ-fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated cholest-5-en-3-one derivative as well as a difluorinated product pertinent to drug discovery.

Key words

fluorine-18 - late-stage fluorination - PET radiochemistry - diazo chemistry - positron emission tomography

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690012.
  • Supporting Information
 

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