Synlett 2019; 30(12): 1371-1376
DOI: 10.1055/s-0037-1611764
synpacts
© Georg Thieme Verlag Stuttgart · New York

Expanding the 18F-Radiochemical Space: Synthesis and Applications of 1,1-18F-Difluorinated Alkenes

We thank the Max-Planck-Institut für Kohlenforschung and Prof. Tobias Ritter for generous support.
Further Information

Publication History

Received: 07 February 2019

Accepted after revision: 28 February 2019

Publication Date:
25 March 2019 (eFirst)

Abstract

The synthesis of 18F-perfluorinated motifs from [18F]fluoride is a non-trivial undertaking as highlighted by the few methods and range of motifs that are known. In this Synpacts article we highlight our recent work on the synthesis and derivatization of 1,1-18F-difluoroalkenes to expand the accessible radiochemical space with fluorine-18.

1 Introduction

2 Overview of the Main Strategies to Access 18F-Perfluorinated Motifs with [18F]Fluoride

3 1,1-18F-Difluoroalkenes

4 Conclusion

 
  • References

  • 1 Harsanyi A, Sandford G. Org. Process Res. Dev. 2014; 18: 981
    • 2a Kniess T, Laube M, Brust P, Steinbach J. Med. Chem. Commun. 2015; 6: 1714
    • 2b van der Born D, Pees A, Poot AJ, Orru RV. A, Windhorst AD, Vugts DJ. Chem. Soc. Rev. 2017; 46: 4709
  • 3 Sanford SM, Scott PJ. H. ACS Cent. Sci. 2016; 2: 128
  • 4 Campbell MG, Mercier J, Genicot C, Gouverneur V, Hooker JM, Ritter T. Nat. Chem. 2017; 9: 1
  • 5 Frost AB, Brambilla M, Exner RM, Tredwell M. Angew. Chem. Int. Ed. 2019; 58: 472

    • For seminal contributions, see:
    • 6a Angelini G, Speranza M, Shiue C.-Y, Wolf AP. J. Chem. Soc., Chem. Commun. 1986; 924
    • 6b Kilbourn MR, Pavia MR, Gregor VE. Appl. Radiat. Isot. 1990; 41: 823
    • 6c Johnström P, Stone-Elander S. J. Labelled Compd. Radiopharm. 1995; 36: 537

      For reviews, see:
    • 7a Brooks AF, Topczewski JJ, Ichiishi N, Sanford MS, Scott PJ. H. Chem. Sci. 2014; 5: 4545
    • 7b Preshlock S, Tredwell M, Gouverneur V. Chem. Rev. 2016; 116: 719
    • 7c Deng X, Rong J, Wang L, Vasdev N, Zhang L, Josephson L, Liang SH. Angew. Chem. Int. Ed. 2019; 58: 2580
  • 8 Lien VT, Riss PJ. BioMed Res. Int. 2014; 380124
    • 9a Riss PJ, Aigbirhio FI. Chem. Commun. 2011; 47: 11873
    • 9b Riss PJ, Ferrari V, Brichard L, Burke P, Smith R, Aigbirhio FI. Org. Biomol. Chem. 2012; 10: 6980
  • 10 Levin MD, Chen TQ, Neubig ME, Hong CM, Theulier CA, Kobylianskii IJ, Janabi M, O’Neil JP, Toste FD. Science 2017; 356: 1272
    • 11a Zheng J, Wang L, Lin JH, Xiao JC, Liang SH. Angew. Chem. Int. Ed. 2015; 54: 13236
    • 11b Zheng J, Cheng R, Lin JH, Yu DH, Ma L, Jia L, Zhang L, Wang L, Xiao JC, Liang SH. Angew. Chem. Int. Ed. 2017; 56: 3196
  • 12 For a detailed study on the synthesis of gem-[18F]difluoroalkenes by isotopic substitution, see: Fawaz MV, Brooks AF, Rodnick ME, Carpenter GM, Shao X, Desmond TJ, Sherman P, Quesada CA, Hockley BG, Kilbourn MR, Albin RL, Frey KA, Scott PJ. H. ACS Chem. Neurosci. 2014; 5: 718
    • 13a Zhang X, Cao S. Tetrahedron Lett. 2017; 58: 375
    • 13b Wang F, Li L, Ni C, Hu J. Beilstein J. Org. Chem. 2014; 10: 344 ; and references therein
    • 14a McDonald IA, Lacoste JM, Bey P, Palfreyman MG. Zreika M. J. Med. Chem. 1985; 28: 186
    • 14b Bennett B, Matagne A, Michel P, Leonard M, Cornet M, Meeus M.-A, Toublanc N. Neurotherapeutics 2007; 4: 117
    • 14c Juncosa JI, Takaya K, Le HV, Moschitto MJ, Weerawarna PM, Mascarenhas R, Liu D, Dewey SL, Silverman RB. J. Am. Chem. Soc. 2018; 140: 2151
    • 15a Amii H, Uneyama K. Chem. Rev. 2009; 109: 2119
    • 15b Chelucci G. Chem. Rev. 2012; 112: 1344
  • 16 Okuyama T, Takino T, Sueda T, Ochiai M. J. Am. Chem. Soc. 1995; 117: 3360
  • 17 Ochiai M, Oshima K, Masaki Y. J. Am. Chem. Soc. 1991; 113: 7059