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Synlett 2018; 29(09): 1131-1135
DOI: 10.1055/s-0036-1591948
synpacts
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic 18F-Fluorination of Anilines via N-Arylsydnone Intermediates

Maruthi Kumar Narayanam
a   Department of Molecular and Medical Pharmacology and Crump Institute for Molecular Imaging, David Geffen School of Medicine, University of California, Los Angeles, CA 90095, USA   Email: jmmurphy@mednet.ucla.edu
,
Gaoyuan Ma
a   Department of Molecular and Medical Pharmacology and Crump Institute for Molecular Imaging, David Geffen School of Medicine, University of California, Los Angeles, CA 90095, USA   Email: jmmurphy@mednet.ucla.edu
,
Pier Alexandre Champagne
b   Department of Chemistry and Biochemistry, and Department of Chemical and Biomolecular Engineering, University of California, Los Angeles, CA 90095, USA
,
Kendall N. Houk
b   Department of Chemistry and Biochemistry, and Department of Chemical and Biomolecular Engineering, University of California, Los Angeles, CA 90095, USA
,
Jennifer M. Murphy*
a   Department of Molecular and Medical Pharmacology and Crump Institute for Molecular Imaging, David Geffen School of Medicine, University of California, Los Angeles, CA 90095, USA   Email: jmmurphy@mednet.ucla.edu
› Author AffiliationsThis research was supported by the Jonsson Comprehensive Cancer Center, the Crump Institute for Molecular Imaging, the NIH (R01GM109078) and the FRQNT (post-doctoral fellowship to P.A.C.).
Further Information

Publication History

Received: 11 January 2018

Accepted after revision: 08 February 2018

Publication Date:
26 February 2018 (online)

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Abstract

Preparation of [18F]fluoroarenes with nucleophilic [18F]fluoride for positron emission tomography (PET) molecular imaging ­research is a challenging chemical endeavor. Advances in radiofluorination have soared in the last decade, broadening the availability of potential [18F]fluoroarenes. In this Synpacts article, we highlight the ­recent development from our laboratory of a practical radiofluorination of anilines via N-arylsydnone intermediates to afford [18F]fluoroarenes. Further, we emphasize the utility of this methodology towards peptide labeling applications by preparing an 18F-labeled neuropeptide.

1 Introduction

2 Nucleophilic Radiofluorination of N-Arylsydnones

3 Substrate Scope and Applications

4 Conclusion

Key words

fluorine-18 - sydnone - bioorthogonal chemistry - fluoroarene - peptide labeling