1 Ametamey, S. M., Honer, M. & Schubiger, P. A. Molecular imaging with PET. Chem Rev 108, 1501-1516, doi:10.1021/cr0782426 (2008).
2 Pike, V. W. PET radiotracers: crossing the blood-brain barrier and surviving metabolism. Trends Pharmacol Sci 30, 431-440, doi:10.1016/j.tips.2009.05.005 (2009).
3 Deng, X. Y. et al. Chemistry for Positron Emission Tomography: Recent Advances in C-11-, F-18-, N-13-, and O-15-Labeling Reactions. Angew Chem Int Edit 58, 2580-2605, doi:10.1002/anie.201805501 (2019).
4 Aldeghi, M., Malhotra, S., Selwood, D. L. & Chan, A. W. Two- and three-dimensional rings in drugs. Chem Biol Drug Des 83, 450-461, doi:10.1111/cbdd.12260 (2014).
5 Taylor, R. D., MacCoss, M. & Lawson, A. D. Rings in drugs. J Med Chem 57, 5845-5859, doi:10.1021/jm4017625 (2014).
6 Poleto, M. D. et al. Aromatic Rings Commonly Used in Medicinal Chemistry: Force Fields Comparison and Interactions With Water Toward the Design of New Chemical Entities. Front Pharmacol 9, 395, doi:10.3389/fphar.2018.00395 (2018).
7 Jacobson, O., Kiesewetter, D. O. & Chen, X. Y. Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes. Bioconjugate Chem 26, 1-18, doi:10.1021/bc500475e (2015).
8 Preshlock, S., Tredwell, M. & Gouverneur, V. (18)F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography. Chem Rev 116, 719-766, doi:10.1021/acs.chemrev.5b00493 (2016).
9 van der Born, D. et al. Fluorine-18 labelled building blocks for PET tracer synthesis. Chemical Society Reviews 46, 4709-4773, doi:10.1039/c6cs00492j (2017).
10 Krishnan, H. S., Ma, L. L., Vasdev, N. & Liang, S. H. F-18-Labeling of Sensitive Biomolecules for Positron Emission Tomography. Chem-Eur J 23, 15553-15577, doi:10.1002/chem.201701581 (2017).
11 Ding, Y. S. et al. Synthesis of High Specific Activity 6-[F-18]Fluorodopamine for Positron Emission Tomography Studies of Sympathetic Nervous-Tissue. J Med Chem 34, 861-863, doi:DOI 10.1021/jm00106a055 (1991).
12 Cai, L. S., Lu, S. Y. & Pike, V. W. Chemistry with [F-18]fluoride ion. Eur J Org Chem 2008, 2853-2873, doi:10.1002/ejoc.200800114 (2008).
13 Quednow, B. B. et al. Assessment of serotonin release capacity in the human brain using dexfenfluramine challenge and [F-18]altanserin positron emission tomography. Neuroimage 59, 3922-3932, doi:10.1016/j.neuroimage.2011.09.045 (2012).
14 Cole, E. L., Stewart, M. N., Littich, R., Hoareau, R. & Scott, P. J. H. Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination. Current Topics in Medicinal Chemistry 14, 875-900, doi:Doi 10.2174/1568026614666140202205035 (2014).
15 Adams, D. J. & Clark, J. H. Nucleophilic routes to selectively fluorinated aromatics. Chemical Society Reviews 28, 225-231, doi:DOI 10.1039/a808707e (1999).
16 Brooks, A. F., Topczewski, J. J., Ichiishi, N., Sanford, M. S. & Scott, P. J. Late-stage [(18)F]Fluorination: New Solutions to Old Problems. Chem Sci 5, 4545-4553, doi:10.1039/C4SC02099E (2014).
17 Lee, E. et al. A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging. Science 334, 639-642, doi:10.1126/science.1212625 (2011).
18 Lee, E., Hooker, J. M. & Ritter, T. Nickel-Mediated Oxidative Fluorination for PET with Aqueous [F-18] Fluoride. J Am Chem Soc 134, 17456-17458, doi:10.1021/ja3084797 (2012).
19 Tredwell, M. et al. A General Copper-Mediated Nucleophilic F-18 Fluorination of Arenes. Angew Chem Int Edit 53, 7751-7755, doi:10.1002/anie.201404436 (2014).
20 Ichiishi, N. et al. Copper-Catalyzed [F-18]Fluorination of (Mesityl)(aryl)iodonium Salts. Org Lett 16, 3224-3227, doi:10.1021/ol501243g (2014).
21 Mossine, A. V. et al. Synthesis of [F-18]Arenes via the Copper-Mediated [F-18]Fluorination of Boronic Acids. Org Lett 17, 5780-5783, doi:10.1021/acs.orglett.5b02875 (2015).
22 Makaravage, K. J., Brooks, A. F., Mossine, A. V., Sanford, M. S. & Scott, P. J. H. Copper-Mediated Radiofluorination of Arylstannanes with [F-18]KF. Org Lett 18, 5440-5443, doi:10.1021/acs.orglett.6b02911 (2016).
23 McCammant, M. S. et al. Cu-Mediated C-H F-18-Fluorination of Electron-Rich (Hetero)arenes. Org Lett 19, 3939-3942, doi:10.1021/acs.orglett.7b01902 (2017).
24 Rotstein, B. H., Stephenson, N. A., Vasdev, N. & Liang, S. H. Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics. Nat Commun 5, doi:ARTN 4365
10.1038/ncomms5365 (2014).
25 Sander, K. et al. Sulfonium Salts as Leaving Groups for Aromatic Labelling of Drug-like Small Molecules with Fluorine-18. Sci Rep-Uk 5, doi:ARTN 9941
10.1038/srep09941 (2015).
26 Neumann, C. N., Hooker, J. M. & Ritter, T. Concerted nucleophilic aromatic substitution with F-19(-) and F-18(-) (vol 534, pg 369, 2016). Nature 538, doi:10.1038/nature19311 (2016).
27 Xu, P. et al. Site-Selective Late-Stage Aromatic [F-18]Fluorination via Aryl Sulfonium Salts. Angew Chem Int Edit 59, 1956-1960, doi:10.1002/anie.201912567 (2020).
28 Tay, N. E. S. et al. F-19-and(18)F-arene deoxyfluorination via organic photoredox-catalysed polarity-reversed nucleophilic aromatic substitution. Nat Catal, doi:10.1038/s41929-020-0495-0 (2020).
29 Chun, J. H., Lu, S. Y., Lee, Y. S. & Pike, V. W. Fast and High-Yield Microreactor Syntheses of ortho-Substituted [F-18]Fluoroarenes from Reactions of [F-18]Fluoride Ion with Diaryliodonium Salts. J Org Chem 75, 3332-3338, doi:10.1021/jo100361d (2010).
30 Sharninghausen, L. S. et al. NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides. J Am Chem Soc 142, 7362-7367, doi:10.1021/jacs.0c02637 (2020).
31 Wilcken, R., Zimmermann, M. O., Lange, A., Joerger, A. C. & Boeckler, F. M. Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology. J Med Chem 56, 1363-1388, doi:10.1021/jm3012068 (2013).
32 Zhou, Y. et al. Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas. Chemical Reviews 116, 422-518, doi:10.1021/acs.chemrev.5b00392 (2016).
33 Fang, W. Y. et al. Synthetic approaches and pharmaceutical applications of chloro-containing molecules for drug discovery: A critical review. Eur J Med Chem 173, 117-153, doi:10.1016/j.ejmech.2019.03.063 (2019).
34 Babich, J. W. et al. F-18-labeling and biodistribution of the novel fluoro-quinolone antimicrobial agent, trovafloxacin (CP 99,219). Nucl Med Biol 23, 995-998, doi:Doi 10.1016/S0969-8051(96)00153-9 (1996).
35 Langer, O. et al. Synthesis of fluorine-18-labeled Ciprofloxacin for PET studies in humans. Nucl Med Biol 30, 285-291, doi:10.1016/S0969-8051(02)00444-4 (2003).
36 Rokka, J. et al. F-19/F-18 exchange synthesis for a novel [F-18]S1P(3)-radiopharmaceutical. J Labelled Compd Rad 56, 385-391, doi:10.1002/jlcr.3055 (2013).
37 Chen, W. et al. Direct arene C-H fluorination with F-18(-) via organic photoredox catalysis. Science 364, 1170-+, doi:10.1126/science.aav7019 (2019).
38 Zweig, A., Hodgson, W. G. & Jura, W. H. Oxidation of Methoxybenzenes. J Am Chem Soc 86, 4124-&, doi:DOI 10.1021/ja01073a043 (1964).
39 Wagner, F. M., Ermert, J. & Coenen, H. H. Three-Step, "One-Pot" Radiosynthesis of 6-Fluoro-3,4-Dihydroxy-L-Phenylalanine by Isotopic Exchange. J Nucl Med 50, 1724-1729, doi:10.2967/jnumed.109.063297 (2009).
40 Blom, E., Karimi, F. & Langstrom, B. [F-18]/F-19 exchange in fluorine containing compounds for potential use in F-18-labelling strategies. J Labelled Compd Rad 52, 504-511, doi:10.1002/jlcr.1670 (2009).
41 Weiss, P. S., Ermert, J., Melean, J. C., Schafer, D. & Coenen, H. H. Radiosynthesis of 4-[F-18]fluoro-L-tryptophan by isotopic exchange on carbonyl-activated precursors. Bioorgan Med Chem 23, 5856-5869, doi:10.1016/j.bmc.2015.06.073 (2015).
42 Liu, Z. et al. An organotrifluoroborate for broadly applicable one-step 18F-labeling. Angew Chem Int Ed Engl 53, 11876-11880, doi:10.1002/anie.201406258 (2014).
43 Tay, N. E. S. & Nicewicz, D. A. Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis. J Am Chem Soc 139, 16100-16104, doi:10.1021/jacs.7b10076 (2017).
44 Holmberg-Douglas, N. & Nicewicz, D. A. Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution. Org Lett 21, 7114-7118, doi:10.1021/acs.orglett.9b02678 (2019).
45 Venditto, N. J. & Nicewicz, D. A. Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes. Org Lett 22, 4817-4822, doi:10.1021/acs.orglett.0c01621 (2020).
46 Shewchuk, L. et al. Binding mode of the 4-anilinoquinazoline class of protein kinase inhibitor: X-ray crystallographic studies of 4-anilinoquinazolines bound to cyclin-dependent kinase 2 and p38 kinase. J Med Chem 43, 133-138, doi:DOI 10.1021/jm990401t (2000).
47 Olberg, D. E. et al. Synthesis and in vitro evaluation of small-molecule [F-18] labeled gonadotropin-releasing hormone (GnRH) receptor antagonists as potential PET imaging agents for GnRH receptor expression. Bioorg Med Chem Lett 24, 1846-1850, doi:10.1016/j.bmcl.2014.02.002 (2014).
48 Vivash, L. & O'Brien, T. J. Imaging Microglial Activation with TSPO PET: Lighting Up Neurologic Diseases? J Nucl Med 57, 165-168, doi:10.2967/jnumed.114.141713 (2016).
49 Alam, M. M., Lee, J. & Lee, S. Y. Recent Progress in the Development of TSPO PET Ligands for Neuroinflammation Imaging in Neurological Diseases. Nucl Med Molec Imag 51, 283-296, doi:10.1007/s13139-017-0475-8 (2017).
50 Werry, E. L. et al. Recent Developments in TSPO PET Imaging as A Biomarker of Neuroinflammation in Neurodegenerative Disorders. International Journal of Molecular Sciences 20, doi:ARTN 3161
10.3390/ijms20133161 (2019).
51 Oberdorfer, F., Hofmann, E. & Maierborst, W. Preparation of F-18-Labeled 5-Fluorouracil of Very High-Purity. J Labelled Compd Rad 27, 137-145, doi:DOI 10.1002/jlcr.2580270204 (1989).
52 Hoover, A. J. et al. A Transmetalation Reaction Enables the Synthesis of [F-18]5-Fluorouracil from [F-18]Fluoride for Human PET Imaging. Organometallics 35, 1008-1014, doi:10.1021/acs.organomet.6b00059 (2016).
53 Qi, Y. Q., Liu, X. H., Li, J., Yao, H. Q. & Yuan, S. H. Fluorine-18 labeled amino acids for tumor PET/CT imaging. Oncotarget 8, 60581-60588, doi:10.18632/oncotarget.19943 (2017).
54 Sun, A. X., Liu, X. & Tang, G. H. Carbon-11 and Fluorine-18 Labeled Amino Acid Tracers for Positron Emission Tomography Imaging of Tumors. Front Chem 5, doi:ARTN 124
10.3389/fchem.2017.00124 (2018).
55 Langen, K. J. et al. O-(2-[F-18]fluoroethyl)-L-tyrosine: uptake mechanisms and clinical applications. Nucl Med Biol 33, 287-294, doi:10.1016/j.nucmedbio.2006.01.002 (2006).
56 Stegmayr, C., Willuweit, A., Lohmann, P. & Langen, K. J. O-(2-[F-18]-Fluoroethyl)-L-Tyrosine (FET) in Neurooncology: A Review of Experimental Results. Current Radiopharmaceuticals 12, 201-210, doi:10.2174/1874471012666190111111046 (2019).
57 Franck, D. et al. Investigations into the synthesis, radiofluorination and conjugation of a new [F-18]fluorocyclobutyl prosthetic group and its in vitro stability using a tyrosine model system. Bioorgan Med Chem 21, 643-652, doi:10.1016/j.bmc.2012.11.049 (2013).
58 Kuchar, M. & Mamat, C. Methods to Increase the Metabolic Stability of F-18-Radiotracers. Molecules 20, 16186-16220, doi:10.3390/molecules200916186 (2015).
59 Zoghbi, S. S. et al. PET imaging of the dopamine transporter with F-18-FECNT: A polar radiometabolite confounds brain radioligand measurements. J Nucl Med 47, 520-527 (2006).
60 Lee, S. L. Radioactive iodine therapy. Curr Opin Endocrinol Diabetes Obes 19, 420-428, doi:10.1097/med.0b013e328357fa0c (2012).
61 Barth, R. F., Mi, P. & Yang, W. Boron delivery agents for neutron capture therapy of cancer. Cancer communications (London, England) 38, 35, doi:10.1186/s40880-018-0299-7 (2018).
62 Garnett, E. S., Firnau, G. & Nahmias, C. Dopamine Visualized in the Basal Ganglia of Living Man. Nature 305, 137-138, doi:DOI 10.1038/305137a0 (1983).
63 Pretze, M., Wangler, C. & Wangler, B. 6-[F-18] Fluoro-L-DOPA: A Well-Established Neurotracer with Expanding Application Spectrum and Strongly Improved Radiosyntheses. Biomed Research International 2014, doi:Artn 674063
10.1155/2014/674063 (2014).
64 Mossine, A. V. et al. One-pot synthesis of high molar activity 6-[F-18]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor. Org Biomol Chem 17, 8701-8705, doi:10.1039/c9ob01758e (2019).
65 Preshlock, S. et al. Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications. Chem Commun 52, 8361-8364, doi:10.1039/C6CC03295H (2016).
66 Zarrad, F., Zlatopolskiy, B. D., Krapf, P., Zischler, J. & Neumaier, B. A Practical Method for the Preparation of (18)F-Labeled Aromatic Amino Acids from Nucleophilic [(18)F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules 22, doi:10.3390/molecules22122231 (2017).
67 Luurtsema, G. et al. Improved GMP-compliant multi-dose production and quality control of 6-[(18)F]fluoro-L-DOPA. EJNMMI Radiopharm Chem 1, 7, doi:10.1186/s41181-016-0009-1 (2017).
68 Lemaire, C. et al. Automated production at the curie level of no-carrier-added 6-[(18)F]fluoro-L-dopa and 2-[(18)F]fluoro-L-tyrosine on a FASTlab synthesizer. J Labelled Comp Radiopharm 58, 281-290, doi:10.1002/jlcr.3291 (2015).
69 Luxen, A. et al. Production of 6-[18f]Fluoro-L-Dopa and Its Metabolism Invivo - a Critical-Review. Nucl Med Biol 19, 149-158, doi:Doi 10.1016/0883-2897(92)90002-G (1992).