Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Nature Communications

Volumn 5, Issue , 2014, Pages

  Rotstein, Benjamin H ^a,b   Stephenson, Nickeisha A ^a,b   Vasdev, Neil ^a,b   Liang, Steven H ^a,b  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE 18; POLYCYCLIC AROMATIC HYDROCARBON; AROMATIC HYDROCARBON; FLUORINE; IODINATED HYDROCARBON; IODINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SPIRO COMPOUND;

AROMATIC HYDROCARBON; COMPLEXATION; DRUG DEVELOPMENT; FLUORINE; IODINE; RADIOGRAPHY; RADIONUCLIDE; SUBSTRATE; TECHNOLOGICAL DEVELOPMENT; TOMOGRAPHY;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS COUPLING REACTION; ELECTROPHILICITY; FLUORINATION; ISOTOPE LABELING; NUCLEOPHILICITY; RADIOACTIVITY; RADIOCHEMISTRY; RADIOFLUORINATION; SCALE UP; SUBSTITUTION REACTION; CHEMISTRY; CYCLIZATION; HALOGENATION; POSITRON EMISSION TOMOGRAPHY;

CYCLIZATION; FLUORINE RADIOISOTOPES; HALOGENATION; HYDROCARBONS, AROMATIC; HYDROCARBONS, IODINATED; IODINE COMPOUNDS; ISOTOPE LABELING; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; SPIRO COMPOUNDS;

EID: 84904189361     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms5365     Document Type: Article

References (40)

1. Fowler, J. S. & Wolf, A. P. Working against time: rapid radiotracer synthesis and imaging the human brain. Acc. Chem. Res. 30, 181-188 (1997). (Pubitemid 127472558)
2. Phelps, M. E. Positron emission tomography provides molecular imaging of biological processes. Proc. Natl Acad. Sci. USA 97, 9226-9223 (2000).
3. Ametamey, S. M., Honer, M. & Schubiger, P. A. Molecular imaging with PET. Chem. Rev. 108, 1501-1516 (2008). (Pubitemid 351796395)
4. Cai, L., Lu, S. & Pike, V. W. Chemistry with [18F]fluoride ion. Eur. J. Org. Chem. 2008, 2853-2873 (2008).
5. Miller, P. W., Long, N. J., Vilar, R. & Gee, A. D. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography. Angew. Chem. Int. Ed. 47, 8998-9033 (2008).
6. Holland, J. P. et al. Alternative approaches for PET radiotracer development in Alzheimer's disease: imaging beyond plaque. J. Labelled Compd. Radiopharm. 57, 323-331 (2014).
7. Balz, G. & Schiemann, G. Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung. Ber. dtsch. Chem. Ges. A/B 60, 1186-1190 (1927).
8. Wallach, O. Ueber das Verhalten einiger Diazo-und Diazoamidover- bindungen. Justus Liebigs Ann. Chem. 235, 233-255 (1886).
9. Mu, L. et al. 18F-radiolabeling of aromatic compounds using triarylsulfonium salts. Eur. J. Org. Chem. 2012, 889-892 (2012).
10. Chun, J.-H., Morse, C. L., Chin, F. T. & Pike, V. W. No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides. Chem. Commun. 49, 2151-2153 (2013).
11. 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 (2009).
12. Lee, E., Hooker, J. M. & Ritter, T. Nickel-mediated oxidative fluorination for PET with aqueous [18F] fluoride. J. Am. Chem. Soc. 134, 17456-17458 (2012).
13. Lee, E. et al. A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging. Science 334, 639-642 (2011).
14. Gao, Z. et al. Metal-free oxidative fluorination of phenols with [18F]fluoride. Angew. Chem. Int. Ed. 51, 6733-6737 (2012).
15. Pike, V. W. & Aigbirhio, F. I. 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. 2215-2216 (1995).
16. Shah, A., Pike, V. W. & Widdowson, D. A. The synthesis of [18F]fluoroarenes from the reaction of cyclotron-produced [18F]fluoride ion with diaryliodonium salts. J. Chem. Soc. Perkin Trans. 1 2043-2046 (1998). (Pubitemid 128759646)
17. Ross, T. L., Ermert, J., Hocke, C. & Coenen, H. H. Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride. J. Am. Chem. Soc. 129, 8018-8025 (2007). (Pubitemid 46998201)
18. Yusubov, M. S., Maskaev, A. V. & Zhdankin, V. V. Iodonium salts in organic synthesis. ARKIVOC 2011, 370-409 (2011).
19. Yusubov, M. S., Svitich, D. Y., Larkina, M. S. & Zhdankin, V. V. Applications of iodonium salts and iodonium ylides as precursors for nucleophilic fluorination in positron emission tomography. ARKIVOC 2013, 364-395 (2013).
20. Carroll, M. A., Jones, C. & Tang, S.-L. Fluoridation of 2-thienyliodonium salts. J. Labelled Compd. Radiopharm. 50, 450-451 (2007). (Pubitemid 47309048)
21. Satyamurthy, N. & Barrio, J. R. No-carrier-added nucleophilic [F-18] fluorination of aromatic compounds. WO2010/117435 A2 (2010).
22. Moon, B. S. et al. Facile aromatic radiofluorination of [18F]flumazenil from diaryliodonium salts with evaluation of their stability and selectivity. Org. Biomol. Chem. 9, 8346-8355 (2011).
23. Wang, B., Cerny, R. L., Uppaluri, S., Kempinger, J. J. & Dimagno, S. G. Fluoride-promoted ligand exchange in diaryliodonium salts. J. Fluorine Chem. 131, 1113-1121 (2010).
24. Martin-Santamaria, S. et al. Fluoridation of heteroaromatic iodonium salts-experimental evidence supporting theoretical prediction of the selectivity of the process. Chem. Commun. 649-650 (2000).
25. Graskemper, J. W., Wang, B., Qin, L., Neumann, K. D. & DiMagno, S. G. Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts. Org. Lett. 13, 3158-3161 (2011).
26. Wang, B., Graskemper, J. W., Qin, L. & DiMagno, S. G. Regiospecific reductive elimination from diaryliodonium salts. Angew. Chem. Int. Ed. 49, 4079-4083 (2010).
27. Reed, C. D., Launay, G. G. & Carroll, M. A. Evaluation of tetraethylammonium bicarbonate as a phase-transfer agent in the formation of [18F]fluoroarenes. J. Fluorine Chem. 143, 231-237 (2012).
28. Turkman, N. et al. Synthesis and preliminary evaluation of [18F]-labeled 2-oxoquinoline derivatives for PET imaging of cannabinoid CB2 receptor. Nucl. Med. Biol. 39, 593-600 (2012).
29. Koslowsky, I., Mercer, J. & Wuest, F. Synthesis and application of 4-[18F]fluorobenzylamine: a versatile building block for the preparation of PET radiotracers. Org. Biomol. Chem. 8, 4730-4735 (2010).
30. Pretze, M., GroBe-Gehling, P. & Mamat, C. Cross-coupling reactions as valuable tool for the preparation of PET radiotracers. Molecules 16, 1129-1165 (2011).
31. Vasdev, N. et al. Metabolic stability of 6, 7-dialkoxy-4-(2-, 3-and 4-[18F]fluoroanilino)quinazolines, potential EGFR imaging probes. Bioorg. Med. Chem. 19, 2959-2965 (2011).
32. Basuli, F. et al. A first synthesis of 18F-radiolabeled lapatinib: a potential tracer for positron emission tomographic imaging of ErbB1/ErbB2 tyrosine kinase activity. J. Labelled Compd. Radiopharm. 54, 633-636 (2011).
33. Coenen, H. H., Franken, K., Kling, P. & Stocklin, G. Direct electrophilic radiofluorination of phenylalanine, tyrosine and dopa. Int. J. Radiat. Appl. Instrum. 39, 1243-1250 (1988). (Pubitemid 19005344)
34. Namavari, M., Satyamurthy, N., Phelps, M. E. & Barrio, J. R. Synthesis of 6-[18F] and 4-[18F]fluoro-l-m-tyrosines via regioselective radiofluorodestannylation. Appl. Radiat. Isot. 44, 527-536 (1993). (Pubitemid 23069170)
35. VanBrocklin, H. F. et al. A new precursor for the preparation of 6-[18F]Fluoro-l-m-tyrosine ([18F]FMT): efficient synthesis and comparison of radiolabeling. Appl. Radiat. Isot. 61, 1289-1294 (2004). (Pubitemid 39248951)
36. Lemaire, C., Guillaume, M., Christiaens, L., Palmer, A. J. & Cantineau, R. A new route for the synthesis of [18F]fluoroaromatic substituted amino acids: no carrier added L-p-[18F]fluorophenylalanine. Appl. Radiat. Isot. 38, 1033-1038 (1987). (Pubitemid 18081681)
37. Thonon, D., Kech, C., Paris, J., Lemaire, C. & Luxen, A. New strategy for the preparation of clickable peptides and labeling with 1-(azidomethyl)-4-[18F]-fluorobenzene for PET. Bioconjugate Chem. 20, 817-823 (2009).
38. Campbell-Verduyn, L. S. et al. Strain-promoted copper-free "click" chemistry for 18F radiolabeling of Bombesin. Angew. Chem. Int. Ed. 50, 11117-11120 (2011).
39. Chun, J.-H. & Pike, V. W. Single-step radiosynthesis of "18F-labeled click synthons" from azide-functionalized diaryliodonium salts. Eur. J. Org. Chem. 2012, 4541-4547 (2012).
40. Fowler, J. S., Finn, R. D., Lambrecht, R. M. & Wolf, A. P. The synthesis of 18F-5-fluorouracil. VII. J. Nucl. Med. 14, 63-64 (1973).