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Development of fluorination methodology for carbon-fluorine bond formation: nucleophilic fluorinating reagents in the mid-2000s

  • Bae, Dae Young (Department of Chemistry, Pohang University of Science and Technology) ;
  • Lee, Eunsung (Department of Chemistry, Pohang University of Science and Technology)
  • Received : 2017.12.12
  • Accepted : 2017.12.27
  • Published : 2017.12.30

Abstract

Since carbon-fluorine (C-F) bonds play a key role to improve bioavailability and lipophilicity, they have found commonly in pharmaceuticals, radiopharmaceuticals, agrochemicals, and material science. Advances on the efficient method to introduce fluorine to complex organic molecules are mainly results of development of fluorination reagents and transition metal catalysts. In this mini-review, we want to emphasize two representative nucleophilic fluorinating reagents regarding carbon-fluorine bond formation, which were developed in the mid-2000s.

Keywords

References

  1. O'Hagan D, Schaffrath C, Cobb SL, Hamilton JTG, Murphy CD. Biochemistry: biosynthesis of an organofluorine molecule. Nature 2002;416:279.
  2. Deng H, Ma L, Bandaranayaka N, Qin Z, Mann G, Kyeremeh K, Yu Y, Shepherd T, Naismith JH. Identification of fluorinases from Streptomyces sp MA37, Norcardia brasiliensis, and Actinoplanes sp N902-109 by genome mining. ChemBioChem 2014;15: 364-368. https://doi.org/10.1002/cbic.201300732
  3. 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
  4. Furuya T, Kuttruff CA, Ritter T. Carbon-fluorine bond formation. Curr Opin Drug Discov Devel 2008;11:803-819.
  5. Ruppert I, Shilic K, Volbach W. Die ersten $CF_{3}$-substituierten organyl(chlor)silane Tetrahedron Lett 1984;25:2195-2198. https://doi.org/10.1016/S0040-4039(01)80208-2
  6. Ruff O, Ascher EZ. Die Fluoride der VIII. Gruppe des periodischen Systems. Anorg Allg Chem 1929;183:193-213. https://doi.org/10.1002/zaac.19291830113
  7. Baasner B, Hagemann H Tatlow JC. Methods of Organic Chemistry (Houben-Weyl), Organo-Fluorine Compounds. 4th ed. Thieme Verlag: Stuttgart, 1999; Vol. E10.
  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. Liotta CL, Harris HP. 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
  10. Middleton WJ. New fluorinating reagents. Dialkylaminosulfur fluorides. J Org Chem 1975;40:574-578. https://doi.org/10.1021/jo00893a007
  11. Banks RE, Hasszeldine RN, Latham JV, Young IM. 95. Heterocyclic polyfluoro-compounds. Part VI. Preparation of pentafluoropyridine and chlorofluoropyridines from pentachloropyridine. J Chem Soc 1965;0:594-597.
  12. Banks RE, Tatlow JC. Organofluorine Chemistry: Principles and Commercial Applications; Banks RE, Smart BE, Tatlow JC, Eds. Plenum Press: New York, 1994. Ch 2.
  13. Yoshida Y, Kimura Y. A Convenient Synthesis of Fluorobenzaldehydes by KF/$Ph_4PBr$/18-Crown-6 Reagent System. Chem Lett 1988;17:1355-1358. https://doi.org/10.1246/cl.1988.1355
  14. Christe KO, Wilson WW, Wilson RD, Bau R, Feng, J. 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
  15. Sun H, DiMagno SG. Anhydrous tetrabutylammonium fluoride. J Am Chem Soc 2005;127:2050-2051. https://doi.org/10.1021/ja0440497
  16. Sun H, DiMagno SG. Room-temperature nucleophilic aromatic fluorination: experimental and theoretical studies. Angew Chem Int Ed Engl. 2006;45:2720-2725. https://doi.org/10.1002/anie.200504555
  17. 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.
  18. Suzuki H, Kimura Y. Synthesis of 3,4-difluorobenzonitrile and monofluorobenzonitriles by means of halogenexchange fluorination. J Fluorine Chem 1991;52:341-351. https://doi.org/10.1016/S0022-1139(00)80348-6
  19. 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