Introduction
Diaryliodonium salts are a class of hypervalent iodine (III) reagents that have been known since 1894 (Fig. 1) [14]. Although the term “salt” is commonly used, the T-shaped form shown by X-ray structures illustrates that these iodine (III) compounds have more covalent bond characteristics. “Diaryl-λ3-iodanes” is the nomenclature from IUPAC for this type of molecule [25, 36, 45, 46, 48]. Diaryliodonium salts with tetrafluoroborates, triflates, and tosylates as counter anions are frequently used due to their good solubility in general organic solvents, as well as the lack of nucleophilicity of these anions, compared with halide anion salts.
References
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.
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.
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.
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.
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.
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.
CARROLL, M. A., NAIRNE, J. & WOODCRAFT, J. L. 2007b. Diaryliodonium salts: a solution to 3-[18F]fluoropyridine. J. Labelled Compd. Radiopharm., 50, 452–454.
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.
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.
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.
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.
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.
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.
HARTMANN, C. & MEYER, V. 1894. On a new class of iodine, nitrogen-free organic bases. Chem. Zentralbl., 65 Book 1, 550–551.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
MERRITT, E. A. & OLOFSSON, B. 2009. Diaryliodonium Salts: A Journey from Obscurity to Fame. Angew. Chem., Int. Ed., 48, 9052–9070.
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.
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.
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.
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.
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.
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.
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.
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.
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.
SATYAMURTHY, N. & BARRIO, J. R. 2010. No-carrier-added nucleophilic [18F]-fluorination of aromatic compounds using phenyliodonium ylides. WO2010117435A2.
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.
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.
TREDWELL, M. & GOUVERNEUR, V. 2012. 18F Labeling of Arenes. Angew. Chem., Int. Ed., 51, 11426–11437.
VAN DER PUY, M. 1982. Conversion of diaryliodonium salts to aryl fluorides. J. Fluorine Chem., 21, 385–92.
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.
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.
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.
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.
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.
YUSUBOV, M. S., MASKAEV, A. V. & ZHDANKIN, V. V. 2011. Iodonium salts in organic synthesis. ARKIVOC (Gainesville, FL, U. S.), 370–409.
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.
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.
ZHDANKIN, V. V. & STANG, P. J. 2008. Chemistry of polyvalent iodine. Chem Rev, 108, 5299–358.
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.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer Nature Singapore Pte Ltd.
About this entry
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
Chapter history
-
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
-
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