Journal of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회지)

Korean Society of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회)
권호 표지
DOI QR코드

DOI QR Code

Novel organic catalysts for nucleophilic fluorination including F-18 radiofluorination

  • Na, Hyeon Su (Department of Chemistry and Chemical Engineering, Inha University) ;
  • Kim, Dong Wook (Department of Chemistry and Chemical Engineering, Inha University)
  • Received : 2017.12.11
  • Accepted : 2017.12.24
  • Published : 2017.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

To overcome the low reactivity and solubility of alkali metal fluorides (MFs), various types of phase transfer catalysts (PTCs) have been developed over the last decades. However, since the fluoride activated by such PTC sometimes has a strong basicity, it may cause various side reactions such as elimination reaction or hydroxylation reaction in the nucleophilic fluorination reaction. Also, they may cause separation problems in the compound purification process. In recent advanced study, various PTCs have been developed to solve these problem of conventional catalyst. In this review, we would like to introduce three kinds of novel multifunctional organic catalysts such as bis-tert-alcohol-functionalized crown-6-calix[4]arene (BACCA), easy separable pyrene-tagged ionic liquid (PIL) by reduced graphene oxide (rGO), and tri-tert-butanolamine organic catalyst.

Keywords

References

  1. Ametamey SM, Honer M, Schubiger PA. Molecular imaging with PET. Chem Rev 2008;108:1501-1516 https://doi.org/10.1021/cr0782426
  2. Phelps ME. Positron emission tomography provides molecular imaging of biological processes. Proc Natl Acad Sci USA 2000;97:9226-9233. https://doi.org/10.1073/pnas.97.16.9226
  3. Campbell MG, Ritter T. Modern carbon-fluorine bond forming reactions for aryl fluoride synthesis. Chem Rev 2015;115:612-633 https://doi.org/10.1021/cr500366b
  4. Mascaretti OA. Modern methods for the monofluorination of aliphatic organic compounds. Aldrichimica Acta 1993;26:47-58.
  5. Dehmlow EV, Dehmlow SS. Phase transfer catalysis 3rd ed. VCH Ltd 1993.
  6. Gokel GW. In crown ethers and cryptands. Royal Society of Chemistry 1991 Cambridge.
  7. Pedersen CJ. Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 1967;89:7017-7036. https://doi.org/10.1021/ja01002a035
  8. Gerstenberger MRC, Haas A. Methods of fluorination in organic chemistry. Angew Chem Int Ed 1981;20:647-667 https://doi.org/10.1002/anie.198106471
  9. Pilcher AS, Ammon HL, DeShong P. Utilization of Utilization of Tetrabutylammonium Triphenylsilyldifluoride as a Fluoride Source for Nucleophilic Fluorination. J Am Chem Soc 1995;117:5166-5167. https://doi.org/10.1021/ja00123a025
  10. Welton T. Room-temperature ionic liquids. solvents for synthesis and catalysis. Chem Rev 1999;99:2071-2084.. https://doi.org/10.1021/cr980032t
  11. Kim DW, Song CE, Chi DY. New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity. J Am Chem Soc 2002;124:10278-10279. https://doi.org/10.1021/ja026242b
  12. Jadhav VH, Kim JG, Park SH, Kim DW. Task-specific hexaethylene glycol bridged di-cationic ionic liquids as catalysts for nucleophilic fluorination using potassium fluoride. Chem Eng J 2017;308:664-668. https://doi.org/10.1016/j.cej.2016.09.118
  13. Jadhav VH, Jeong HJ, Lim ST, Sohn MH, Kim DW. Tailor-made hexaethylene glycolic ionic liquids as organic catalysts for specific chemical reactions. Org Lett 2011;13:2502-2505. https://doi.org/10.1021/ol200751e
  14. Kim DW, Chi DY. Polymer-supported ionic liquids: imidazolium salts as catalysts for nucleophilic substitution reactions including fluorinations. Angew Chem Int Ed Engl. 2004;43:483-485. https://doi.org/10.1002/anie.200352760
  15. Kim DW, Ahn DS, Oh YH, Lee S, Oh SJ, Lee SJ, Kim JS, Ryu JS, Moon DH, Chi DY. A new class of SN2 reactions catalyzed by protic solvents; facile fluorination for isotopic labeling of diagnostic molecules. J Am Chem Soc 2006;128:16394-16397 https://doi.org/10.1021/ja0646895
  16. KimDW, JeongHJ, LimST, SohnMH. Tetrabutylammonium tetra(tert-butyl alcohol)-coordinated fluoride as a facile fluoride source. Angew Chem Int Ed Engl. 2008;47:8404- 8406. https://doi.org/10.1002/anie.200803150
  17. O'Hagan D, Deng H. Enzymatic fluorination and biotechnological developments of the fluorinase. Chem Rev 2015;115:634-649. https://doi.org/10.1021/cr500209t
  18. Sessler JL, Kim SK, Gross DE, Lee CH, Kim JS, Lynch VM. Crown-6-calix[4]arene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions. J Am Chem Soc 2008;130:13162-13166. https://doi.org/10.1021/ja804976f
  19. Jadhav VH, Choi W, Lee SS, Lee S, Kim DW. Bis-tert- Alcohol-Functionalized Crown-6-Calix[4]arene: An Organic Promoter for Nucleophilic Fluorination. Chemistry. 2016;22:4515-4520. https://doi.org/10.1002/chem.201504602
  20. Loh KP, Bao Q, Eda G, Chhowalla M. Graphene oxide as a chemically tunable platform for optical applications. Nat Chem 2010;2:1015-1024. https://doi.org/10.1038/nchem.907
  21. Sabater S, Mata JA, Peris E. Catalyst enhancement and recyclability by immobilization of metal complexes onto graphene surface by noncovalent interactions. ACS Catal 2014;4:2038-2047. https://doi.org/10.1021/cs5003959
  22. Dougherty DA. Cation-pi interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp. Science 1996;271:163-168. https://doi.org/10.1126/science.271.5246.163
  23. Taher A, Lee KC, Han HJ, Kim DW. Pyrene-tagged ionic liquids: separable organic catalysts for SN2 fluorination. Org Lett 2017;19:3342−3345. https://doi.org/10.1021/acs.orglett.7b01064
  24. Shinde SS, Khonde NS, Kumar P. Tri-tert-Butanolamine as an Organic Promoter in Nucleophilic Fluorination. ChemistrySelect 2017;2:118-122. https://doi.org/10.1002/slct.201601735