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 Affiliations
This 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)

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

 
  • References

  • 1 Ametamey SM. Honer M. Schubiger PA. Chem. Rev. 2008; 108: 1501
    • 2a Fowler JS. Wolf AP. Acc. Chem. Res. 1997; 30: 181
    • 2b Phelps ME. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 9226
    • 2c Cai L. Lu S. Pike VW. Eur. J. Org. Chem. 2008; 2853
  • 3 Preshlock S. Tredwell M. Gouverneur V. Chem. Rev. 2016; 116: 719
  • 4 Campbell MG. Ritter T. Chem. Rev. 2015; 115: 612
  • 5 Rotstein BH. Stephenson NA. Vasdev N. Liang SH. Nat. Commun. 2014; 5: 4365
  • 6 Petersen IN. Kristensen JL. Herth MM. Eur. J. Org. Chem. 2017; 453
  • 7 Neumann CN. Hooker JM. Ritter T. Nature 2016; 534: 369
  • 8 Narayanam MK. Ma G. Champagne PA. Houk KN. Murphy JM. Angew. Chem. Int. Ed. 2017; 56: 13006
    • 9a Specklin S. Decuypere E. Plougastel L. Aliani S. Taran F. J. Org. Chem. 2014; 79: 7772
    • 9b Plougastel L. Koniev O. Specklin S. Decuypere E. Creminon C. Buisson D.-A. Wagner A. Kolodych S. Taran F. Chem. Commun. 2014; 50: 9376
  • 10 Zhao Y. Truhlar DG. Theor. Chem. Acc. 2008; 120: 215
    • 11a Kolodych S. Rasolofonjatovo E. Chaumontet M. Nevers M.-C. Créminon C. Taran F. Angew. Chem. Int. Ed. 2013; 52: 12056
    • 11b Wallace S. Chin JW. Chem. Sci. 2014; 5: 1742
    • 11c Narayanam MK. Liang Y. Houk KN. Murphy JM. Chem. Sci. 2016; 7: 1257
    • 11d Liu H. Audisio D. Plougastel L. Decuypere E. Buisson D.-A. Koniev O. Kolodych S. Wagner A. Elhabiri M. Krzyczmonik A. Forsback S. Solin O. Gouverneur V. Taran F. Angew. Chem. Int. Ed. 2016; 55: 12073
  • 12 Pretze M. Pietzsch D. Mamat C. Molecules 2013; 18: 8618