Journal of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회지)

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

DOI QR Code

About naked fluoride

  • Lee, Eunsung (Department of Chemistry, Pohang University of Science and Technology)
  • Received : 2018.12.21
  • Accepted : 2018.12.26
  • Published : 2018.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

Fluoride is one of most important atoms for both clinical and pharmaceutical usage. Associated with such a strong need, $^{18}F$-fluoride has been widely used as an essential radioisotope. The fluoride always suffers from strong solvation effects through strong hydrogen bonding, which reduce the reactivity of fluoride anion. To enhance the reactivity, the concept of naked fluoride was introduced in the fluorination field. In this essay, I will briefly describe the history of naked fluoride concept and development of naked fluoride sources.

Keywords

DHBSB1_2018_v4n2_121_f0001.png 이미지

Figure 1. 벌거벗은 불소의 역사 및 대표적인 예시들

References

  1. (a) Wang J, Sanchez-Rosello M, Acena JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chem Rev 2014;114:2432-2506. https://doi.org/10.1021/cr4002879
  2. (b) Ilardi EA, Vitaku E, Njardarson JT. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery. J Med Chem 2014;57:2832-2842. https://doi.org/10.1021/jm401375q
  3. (c) Jeschke P. The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection. ChemBioChem 2004;5:570-589. https://doi.org/10.1002/cbic.200300833
  4. O'Hagan D. Understanding organofluorine chemistry. An introduction to the C-F bond. Chem Soc Rev 2008;37:308-319. https://doi.org/10.1039/B711844A
  5. Konrad S. Does the Naked Fluoride Ion Exist? Angew Chem Int Ed 1992;31:292-293. https://doi.org/10.1002/anie.199202921
  6. Liotta CL, Harris HP. The Chemistry of "Naked" Anions. I. Reactions of the 18-Crown-6 Complex of Potassium Fluoride with Organic Substrates in Aprotic Organic Solvents. J Am Chem Soc 1974;96:2250-2252. https://doi.org/10.1021/ja00814a044
  7. Sharma RK, Fry JL. Instability of Anhydrous Tetra-n-alkylammonium Fluorides. J Org Chem 1983;48:2112-2114. https://doi.org/10.1021/jo00160a041
  8. Christe KO, Wilson WW, Wilson RD, Bau R, Feng JA. Syntheses, Properties, and Structures of Anhydrous Tetramethylammonium Fluoride and Its 1 : 1 Adduct with trans-3-Amino-2-butenenitrile. J Am Chem Soc 1990;112:7619-7625. https://doi.org/10.1021/ja00177a025
  9. Schwesinger R, Link R, Thiele G, Rotter H, Honert D, Limbach HH, Miinnle F. Stable Phosphazenium Ions in Synthesis-an Easily Accessible, Extremely Reactive"Naked" Fluoride Salt? Angew Chem Int Ed 1991;30:1372-1375. https://doi.org/10.1002/anie.199113721
  10. (a) Sun H, DiMagno SG. Anhydrous Tetrabutylammonium Fluoride. J Am Chem Soc 2005;127:2050-2051. https://doi.org/10.1021/ja0440497
  11. (b) Sun H, DiMagno SG. Room-Temperature Nucleophilic Aromatic Fluorination: Experimental and Theoretical Studies. Angew Chem Int Ed 2006;45:2720-2725. https://doi.org/10.1002/anie.200504555
  12. (c) Sun H, DiMagno SG. Fluoride relay: a new concept for the rapid preparation of anhydrous nucleophilic fluoride salts from KF. Chem Commun 2007;5:528-529.
  13. Kim DW, Jeong HJ, Lim ST, Sohn MH. Tetrabutylammonium Tetra(tert-Butyl Alcohol)-Coordinated Fluoride as a Facile Fluoride Source. Angew Chem Int Ed 2008;47:8404-8406. https://doi.org/10.1002/anie.200803150
  14. Ryan SJ, Schimler SD, Bland DC, Sanford MS. Acyl Azolium Fluorides for Room Temperature Nucleophilic Aromatic Fluorination of Chloro- and Nitroarenes. Org Lett 2015;17:1866-1869. https://doi.org/10.1021/acs.orglett.5b00538
  15. Cismesia MA, Ryan SJ, Bland DC, Sanford MS. Multiple Approaches to the In Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions. J Org Chem 2017;82:5020-5026. https://doi.org/10.1021/acs.joc.7b00481