Fluorous Methods for Synthesis and Separation of Organic Molecules: From Separating Mixtures to Making Mixtures

  • Dennis P. Curran
Part of the American Peptide Symposia book series (APSY, volume 7)


Fluorous molecules partition out of an organic phase and into a fluorous (highly fluorinated) phase in a liquid-liquid extraction. New fluorous techniques allow simple yet substantive separations of organic reaction mixtures based on the presence or absence of a fluorous tag. Fluorous-tagged molecules can also be separated from non-tagged molecules by solid phase extraction over fluorous reverse phase silica gel. This technique is ideal for solution phase parallel synthesis because it allows simple yet substantive separations of organic reaction mixtures.


Solid Phase Synthesis Fluorine Content Mixture Synthesis Substantive Separation American Peptide Society 
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  1. 1.
    D.P. Curran, “Combinatorial organic synthesis and phase separation: Back to the future”, Chemtracts-Org. Chem. 9, 75–87 (1996).Google Scholar
  2. 2.
    D.P. Curran, “Strategy-level separations in organic synthesis: From planning to practice”, Angew. Chem., Int. Ed. Engl. 37, 1175–1196 (1998).CrossRefGoogle Scholar
  3. 3.
    J.J. Maul, P.J. Ostrowski, G.A. Ublacker, B. Linclau, D.P. Curran “Benzotrifluoride and related solvents in organic synthesis”, In P. Knochel (Ed.), Topics in Current Chemistry, Modern Solvents in Organic Synthesis. Vol. 206, Springer-Verlag, Berlin, 1999, pp. 80–104.Google Scholar
  4. 4.
    D.P. Curran, “Parallel synthesis with fluorous reagents and reactants”, Med. Res. Rev. 19, 432–438 (1999).PubMedCrossRefGoogle Scholar
  5. 5.
    D.P. Curran, “Fluorous techniques for the synthesis of organic molecules: A unified strategy for reaction and separation”, In Stimulating Concepts in Chemistry, F. Stoddart, D. Reinhoudt, M. Shibasaki, (Eds.), Wiley-VCH, 2000, pp. 25–37.Google Scholar
  6. 6.
    D.P. Curran, “Fluorous methods for synthesis and separation of organic molecules” Pure Appl. Chem. 72, 1649–1653 (2000).CrossRefGoogle Scholar
  7. 7.
    Curran, D.P., Hadida, S., Studer, A., He, M., Kim, S.-Y., Luo, Z., Larhed, M., Hallberg, M., Linclau, B. “Experimental techniques in fluorous synthesis: A user’s guide” In H. Fenniri (Ed.) Combinatorial Chemistry: A Practical Approach; Vol. 2; Oxford Univ Press, Oxford, 2000, pp. 327–352.Google Scholar

Issued Patents

  1. 8.
    Curran, D.P., Hadida, S., Hoshino, M., Studer, A. “Fluorous Reaction Systems”, US 5777121, 1998;Google Scholar
  2. 8a.
    Curran, D.P., Hadida, S., Hoshino, M., Studer, A., Kim, S.-Y., Wipf, P., Jäger, P. “Fluorous Reaction and Separation Systems”, US 5859247, 1999;Google Scholar
  3. 8b.
    Curran, D.P., Hadida, S., Hoshino, M., Studer, A., Kim, S.-Y., Wipf, P., Jäger, P. “Fluorous Reaction and Separation Systems”, US 6156896, 2000.Google Scholar

Fluorous Biphasic Catalysis

  1. 9.
    I.T. Horvath, J. Rabai “Facile catalyst separation without water: Fluorous biphase hydroformylation of olefins”, Science 266, 72–75 (1994).PubMedCrossRefGoogle Scholar
  2. 10.
    I.T. Horvath “Fluorous biphase chemistry”, Acc. Chem. Res. 31, 641–650 (1998).CrossRefGoogle Scholar
  3. 11.
    Dinh, L.V., Gladysz, J.A. Tetrahedron Lett. 40, 8995 (1999).CrossRefGoogle Scholar
  4. 12.
    Y. Nakamura, S. Takeuchi, Y. Ohgo, D.P. Curran, “Asymmetric alkylation of aromatic aldehydes with diethylzinc catalyzed by a fluorous BINOL-Ti complex in an organic and fluorous biphase system”, Tetrahedron Lett. 41, 57–60 (2000).CrossRefGoogle Scholar
  5. 13.
    Y. Nakamura, S. Takeuchi, Y. Ohgo, D.P. Curran, “Preparation of a fluorous chiral BINOL derivative and application to an asymmetric protonation reaction” Tetrahedron 56, 351–356 (2000).CrossRefGoogle Scholar

Fluorous Reagents

  1. 14.
    D.P. Curran, S. Hadida, “Tris(2-(perfluorohexyl)ethyl)tin hydride: A new fluorous reagent for use in traditional organic synthesis and liquid phase combinatorial synthesis”, J. Am. Chem. Soc. 118, 2531–2532 (1996).CrossRefGoogle Scholar
  2. 15.
    D.P. Curran, S. Hadida, S.Y. Kim, Z.Y. Luo, “Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions”, J. Am. Chem. Soc. 121, 6607–6615 (1999).CrossRefGoogle Scholar
  3. 16.
    B. Bucher, D.P. Curran, “Selective sulfonylation of 1, 2-diols and derivatives catalyzed by a recoverable fluorous tin oxide” Tetrahedron Lett. 41, 9617–9621 (2000).CrossRefGoogle Scholar
  4. 17.
    Q. Zhang, Z.Y. Luo, D.P. Curran, “Separation of ‘light fluorous’ reagents and catalysts by fluorous solid-phase extraction: Synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags” J. Org. Chem. 65, 8866–8873 (2000).PubMedCrossRefGoogle Scholar

Fluorous Synthesis

  1. 18.
    A. Studer, S. Hadida, R. Ferritto, S.Y. Kim, P. Jeger, P. Wipf, D.P. Curran, “Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis”, Science 275, 823–826 (1997).PubMedCrossRefGoogle Scholar
  2. 19.
    D.P. Curran, Z.Y. Luo, “Fluorous synthesis with fewer fluorines (Light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel”, J. Am. Chem. Soc. 121, 9069–9072 (1999).CrossRefGoogle Scholar

Fluorous Mixture Synthesis

  1. 20.
    Z. Luo, D.P. Curran, Y. Oderaotoshi, Q. Zhang, “Fluorous mixture synthesis: A fluorous-tagging strategy for synthesis and separation of mixtures of organic compounds”, Science 291, 1766–1769 (2001).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2001

Authors and Affiliations

  • Dennis P. Curran
    • 1
  1. 1.Department of ChemistryUniversity of PittsburghPittsburghUSA

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