Skip to main content

Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides

  • Living reference work entry
  • Latest version View entry history
  • First Online:
Book cover Fluorination

Part of the book series: Synthetic Organofluorine Chemistry ((SYOC))

  • 674 Accesses

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

References

  1. BASULI, F., WU, H. & GRIFFITHS, G. L. 2011. Syntheses of meta-[18F]fluorobenzaldehyde and meta-[18F]fluorobenzyl bromide from phenyl(3-formylphenyl)iodonium salt precursors. J. Labelled Compd. Radiopharm., 54, 224–228.

    Article  CAS  Google Scholar 

  2. BIELAWSKI, M., AILI, D. & OLOFSSON, B. 2008. Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides. J. Org. Chem., 73, 4602–4607.

    Article  CAS  Google Scholar 

  3. BIELAWSKI, M., MALMGREN, J., PARDO, L. M., WIKMARK, Y. & OLOFSSON, B. 2014. One-Pot Synthesis and Applications of N-Heteroaryl Iodonium Salts. ChemistryOpen, 3, 19–22.

    Article  CAS  Google Scholar 

  4. CAMPBELL, M. G. & RITTER, T. 2015. Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis. Chem. Rev. (Washington, DC, U. S.), 115, 612–633.

    Article  CAS  Google Scholar 

  5. CARRERAS, V., SANDTORV, A. H. & STUART, D. R. 2017. Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts. J. Org. Chem., 82, 1279–1284.

    Article  CAS  Google Scholar 

  6. CARROLL, M. A., NAIRNE, J., SMITH, G. & WIDDOWSON, D. A. 2007a. Radical scavengers: A practical solution to the reproducibility issue in the fluoridation of diaryliodonium salts. J. Fluorine Chem., 128, 127–132.

    Article  CAS  Google Scholar 

  7. CARROLL, M. A., NAIRNE, J. & WOODCRAFT, J. L. 2007b. Diaryliodonium salts: a solution to 3-[18F]fluoropyridine. J. Labelled Compd. Radiopharm., 50, 452–454.

    Article  CAS  Google Scholar 

  8. CHUN, J.-H., LU, S., LEE, Y.-S. & PIKE, V. W. 2010. Fast and High-Yield Microreactor Syntheses of ortho-Substituted [18F]Fluoroarenes from Reactions of [18F]Fluoride Ion with Diaryliodonium Salts. J. Org. Chem., 75, 3332–3338.

    Article  CAS  Google Scholar 

  9. CHUN, J.-H., LU, S. & PIKE, V. W. 2011. Rapid and Efficient Radiosyntheses of meta-Substituted [18F]Fluoroarenes from [18F]Fluoride Ion and Diaryliodonium Tosylates within a Microreactor. Eur. J. Org. Chem., 2011, 4439–4447, S4439/1-S4439/67.

    Google Scholar 

  10. CHUN, J.-H. & PIKE, V. W. 2012. Single-Step Radiosynthesis of “18F-Labeled Click Synthons” from Azide-Functionalized Diaryliodonium Salts. Eur. J. Org. Chem., 2012, 4541–4547, S4541/1-S4541/18.

    Google Scholar 

  11. CHUN, J.-H. & PIKE, V. W. 2013. Single-step syntheses of no-carrier-added functionalized [18F]fluoroarenes as labeling synthons from diaryliodonium salts. Org. Biomol. Chem., 11, 6300–6306.

    Article  CAS  Google Scholar 

  12. EDWARDS, R., WESTWELL, A. D., DANIELS, S. & WIRTH, T. 2015. Convenient Synthesis of Diaryliodonium Salts for the Production of [18F]F-DOPA. Eur. J. Org. Chem., 2015, 625–630.

    Google Scholar 

  13. ERMERT, J., HOCKE, C., LUDWIG, T., GAIL, R. & COENEN, H. H. 2004. Comparison of pathways to the versatile synthon of no-carrier-added 1-bromo-4-[18F]fluorobenzene. J. Labelled Compd. Radiopharm., 47, 429–441.

    Article  CAS  Google Scholar 

  14. HARTMANN, C. & MEYER, V. 1894. On a new class of iodine, nitrogen-free organic bases. Chem. Zentralbl., 65 Book 1, 550–551.

    Google Scholar 

  15. HELFER, A., CASTILLO MELEAN, J., ERMERT, J., INFANTINO, A. & COENEN, H. H. 2013. Bis(4-benzyloxyphenyl)iodonium salts as effective precursors for the no-carrier-added radiosynthesis of 4-[18F]fluorophenol. Appl. Radiat. Isot., 82, 264–267.

    Article  CAS  Google Scholar 

  16. HOSSAIN, M. D., IKEGAMI, Y. & KITAMURA, T. 2006. Reaction of arenes with iodine in the presence of potassium peroxodisulfate in trifluoroacetic acid. Direct and simple synthesis of diaryliodonium triflates. J. Org. Chem., 71, 9903–9905.

    Article  CAS  Google Scholar 

  17. ICHIISHI, N., BROOKS, A. F., TOPCZEWSKI, J. J., RODNICK, M. E., SANFORD, M. S. & SCOTT, P. J. H. 2014. Copper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium Salts. Org. Lett., 16, 3224–3227.

    Article  CAS  Google Scholar 

  18. ICHIISHI, N., CANTY, A. J., YATES, B. F. & SANFORD, M. S. 2013. Cu-Catalyzed Fluorination of Diaryliodonium Salts with KF. Org. Lett., 15, 5134–5137.

    Article  CAS  Google Scholar 

  19. JANG, K. S., JUNG, Y.-W., GU, G., KOEPPE, R. A., SHERMAN, P. S., QUESADA, C. A. & RAFFEL, D. M. 2013. 4-[18F]Fluoro-m-hydroxyphenethylguanidine: A Radiopharmaceutical for Quantifying Regional Cardiac Sympathetic Nerve Density with Positron Emission Tomography. J. Med. Chem., 56, 7312–7323.

    Article  CAS  Google Scholar 

  20. KIM, J., MOON, B. S., LEE, B. C., LEE, H.-Y., KIM, H.-J., CHOO, H., PAE, A. N., CHO, Y. S. & MIN, S.-J. 2017. A Potential PET Radiotracer for the 5-HT2C Receptor: Synthesis and in Vivo Evaluation of 4-(3-[18F]fluorophenethoxy)pyrimidine. ACS Chem. Neurosci., Ahead of Print.

    Google Scholar 

  21. KUIK, W.-J., KEMA, I. P., BROUWERS, A. H., ZIJLMA, R., NEUMANN, K. D., DIERCKX, R. A. J. O., DI MAGNO, S. G. & ELSINGA, P. H. 2015. In vivo biodistribution of no-carrier-added 18FDOPA, produced by a new nucleophilic substitution approach, compared with carrier-added 18FDOPA, prepared by conventional electrophilic substitution. J. Nucl. Med., 56, 106–112.

    Article  CAS  Google Scholar 

  22. LANCER, K. M. & WIEGAND, G. H. 1976. The ortho effect in the pyrolysis of iodonium halides. A case for a sterically controlled nucleophilic aromatic (SN) substitution reaction. J. Org. Chem., 41, 3360–4.

    Article  CAS  Google Scholar 

  23. LIBERT, L. C., FRANCI, X., PLENEVAUX, A. R., OOI, T., MARUOKA, K., LUXEN, A. J. & LEMAIRE, C. F. 2013. Production at the Curie level of no-carrier-added 6-18F-fluoro-L-dopa. J. Nucl. Med., 54, 1154–1161.

    Article  CAS  Google Scholar 

  24. LINSTAD, E. J., VAVERE, A. L., HU, B., KEMPINGER, J. J., SNYDER, S. E. & DIMAGNO, S. G. 2017. Thermolysis and radiofluorination of diaryliodonium salts derived from anilines. Org. Biomol. Chem., 15, 2246–2252.

    Article  CAS  Google Scholar 

  25. MERRITT, E. A. & OLOFSSON, B. 2009. Diaryliodonium Salts: A Journey from Obscurity to Fame. Angew. Chem., Int. Ed., 48, 9052–9070.

    Article  CAS  Google Scholar 

  26. MILLER, P. W., LONG, N. J., VILAR, R. & GEE, A. D. 2008. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography. Angew. Chem., Int. Ed., 47, 8998–9033.

    Article  CAS  Google Scholar 

  27. MOON, B. S., KIL, H. S., PARK, J. H., KIM, J. S., PARK, J., CHI, D. Y., LEE, B. C. & KIM, S. E. 2011. Facile aromatic radiofluorination of [18F]flumazenil from diaryliodonium salts with evaluation of their stability and selectivity. Org. Biomol. Chem., 9, 8346–8355.

    Article  CAS  Google Scholar 

  28. MU, L., MULLER HERDE, A., RUEFLI, P. M., SLADOJEVICH, F., MILICEVIC SEPHTON, S., KRAMER, S. D., THOMPSON, A. J., SCHIBLI, R., AMETAMEY, S. M. & LOCHNER, M. 2016. Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging. ACS Chem. Neurosci., 7, 1552–1564.

    Article  CAS  Google Scholar 

  29. NEUMANN, K. D., QIN, L., VAVERE, A. L., SHEN, B., MIAO, Z., CHIN, F. T., SHULKIN, B. L., SNYDER, S. E. & DI MAGNO, S. G. 2016. Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor. J. Labelled Compd. Radiopharm., 59, 30–34.

    Article  CAS  Google Scholar 

  30. PIKE, V. W. & AIGBIRHIO, F. I. 1995. Reactions of cyclotron-produced [18F]fluoride with diaryliodonium salts - a novel single-step route to no-carrier-added [18]fluoroarenes. J. Chem. Soc., Chem. Commun., 2215–6.

    Google Scholar 

  31. PRESHLOCK, S., TREDWELL, M. & GOUVERNEUR, V. 2016. 18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography. Chem. Rev. (Washington, DC, U. S.), 116, 719–766.

    Article  CAS  Google Scholar 

  32. QIN, L., HU, B., NEUMANN, K. D., LINSTAD, E. J., MCCAULEY, K., VENESS, J., KEMPINGER, J. J. & DIMAGNO, S. G. 2015. A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts. Eur. J. Org. Chem., 2015, 5919–5924.

    Article  CAS  Google Scholar 

  33. ROSS, T. L., ERMERT, J., HOCKE, C. & COENEN, H. H. 2007. Nucleophilic 18F-Fluorination of Heteroaromatic Iodonium Salts with No-Carrier-Added [18F]Fluoride. J. Am. Chem. Soc., 129, 8018–8025.

    Article  CAS  Google Scholar 

  34. ROTSTEIN, B. H., STEPHENSON, N. A., VASDEV, N. & LIANG, S. H. 2014. Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics. Nat. Commun., 5, 4365.

    Article  CAS  Google Scholar 

  35. SATYAMURTHY, N. & BARRIO, J. R. 2010. No-carrier-added nucleophilic [18F]-fluorination of aromatic compounds using phenyliodonium ylides. WO2010117435A2.

    Google Scholar 

  36. SOLDATOVA, N., POSTNIKOV, P., KUKURINA, O., ZHDANKIN, V. V., YOSHIMURA, A., WIRTH, T. & YUSUBOV, M. S. 2017. Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone. ChemistryOpen, 6, 18–20.

    Article  CAS  Google Scholar 

  37. TELU, S., CHUN, J.-H., SIMEON, F. G., LU, S. & PIKE, V. W. 2011. Syntheses of mGluR5 PET radioligands through the radiofluorination of diaryliodonium tosylates. Org. Biomol. Chem., 9, 6629–6638.

    Article  CAS  Google Scholar 

  38. TREDWELL, M. & GOUVERNEUR, V. 2012. 18F Labeling of Arenes. Angew. Chem., Int. Ed., 51, 11426–11437.

    Article  CAS  Google Scholar 

  39. VAN DER PUY, M. 1982. Conversion of diaryliodonium salts to aryl fluorides. J. Fluorine Chem., 21, 385–92.

    Article  Google Scholar 

  40. WANG, B., QIN, L., NEUMANN, K. D., UPPALURI, S., CERNY, R. L. & DI MAGNO, S. G. 2010. Improved Arene Fluorination Methodology for I(III) Salts. Org. Lett., 12, 3352–3355.

    Article  CAS  Google Scholar 

  41. WARNIER, C., LEMAIRE, C., BECKER, G., ZARAGOZA, G., GIACOMELLI, F., AERTS, J., OTABASHI, M., BAHRI, M. A., MERCIER, J., PLENEVAUX, A. & LUXEN, A. 2016. Enabling Efficient Positron Emission Tomography (PET) Imaging of Synaptic Vesicle Glycoprotein 2A (SV2A) with a Robust and One-Step Radiosynthesis of a Highly Potent 18F-Labeled Ligand ([18F]UCB-H). J. Med. Chem., 59, 8955–8966.

    Article  CAS  Google Scholar 

  42. WUEST, F. R., HOEHNE, A. & METZ, P. 2005. Synthesis of 18F-labeled cyclooxygenase-2 (COX-2) inhibitors via Stille reaction with 4-[18F]fluoroiodobenzene as radiotracers for positron emission tomography (PET). Org. Biomol. Chem., 3, 503–507.

    Article  CAS  Google Scholar 

  43. WUEST, F. R. & KNIESS, T. 2003. Synthesis of 4-[18F]fluoroiodobenzene and its application in Sonogashira cross-coupling reactions. J. Labelled Compd. Radiopharm., 46, 699–713.

    Article  CAS  Google Scholar 

  44. YAMADA, Y. & OKAWARA, M. 1972. Steric effect in the nucleophilic attack of bromide anion on diaryl- and aryl-2-thienyliodonium ions. Bull. Chem. Soc. Jap., 45, 1860–3.

    Article  CAS  Google Scholar 

  45. YUSUBOV, M. S., MASKAEV, A. V. & ZHDANKIN, V. V. 2011. Iodonium salts in organic synthesis. ARKIVOC (Gainesville, FL, U. S.), 370–409.

    Google Scholar 

  46. YUSUBOV, M. S., SVITICH, D. Y., LARKINA, M. S. & ZHDANKIN, V. V. 2013. Applications of iodonium salts and iodonium ylides as precursors for nucleophilic fluorination in Positron Emission Tomography. ARKIVOC (Gainesville, FL, U. S.), 364–395, 32 pp.

    Google Scholar 

  47. ZHANG, M.-R., KUMATA, K. & SUZUKI, K. 2007. A practical route for synthesizing a PET ligand containing [18F]fluorobenzene using reaction of diphenyliodonium salt with [18F]F. Tetrahedron Lett., 48, 8632–8635.

    Article  CAS  Google Scholar 

  48. ZHDANKIN, V. V. & STANG, P. J. 2008. Chemistry of polyvalent iodine. Chem Rev, 108, 5299–358.

    Article  CAS  Google Scholar 

  49. ZLATOPOLSKIY, B. D., ZISCHLER, J., KRAPF, P., ZARRAD, F., URUSOVA, E. A., KORDYS, E., ENDEPOLS, H. & NEUMAIER, B. 2015. Copper-Mediated Aromatic Radiofluorination Revisited: Efficient Production of PET Tracers on a Preparative Scale. Chem. - Eur. J., 21, 5972–5979.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Wenchao Qu or Ximin Li .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer Nature Singapore Pte Ltd.

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Qu, W., Li, X. (2018). Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_12-2

Download citation

  • DOI: https://doi.org/10.1007/978-981-10-1855-8_12-2

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Singapore

  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics

Chapter history

  1. Latest

    Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides
    Published:
    09 January 2018

    DOI: https://doi.org/10.1007/978-981-10-1855-8_12-2

  2. Original

    Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides
    Published:
    29 September 2017

    DOI: https://doi.org/10.1007/978-981-10-1855-8_12-1