Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis

  • Armido Studer
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Sabine Hadida
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Rafael Ferritto
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Sun-Young Kim
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Patrick Jeger
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Peter Wipf
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
  • Dennis P. Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.

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Description

<jats:p>Recovery and purification difficulties can limit the yield and utility of otherwise successful organic synthesis strategies. A “fluorous synthesis” approach is outlined in which organic molecules are rendered soluble in fluorocarbon solvents by attachment of a suitable fluorocarbon group. Fluorocarbon solvents are usually immiscible in organic solutions, and fluorous molecules partition out of an organic phase and into a fluorous phase in a standard liquid-liquid extraction. Simple yet substantive separations of organic reaction mixtures are achieved without resorting to chromatography. Because fluorous synthesis combines in many respects the favorable purification features of solid-phase synthesis with the favorable reaction, identification, and analysis features of traditional organic synthesis, it should prove valuable in the automated synthesis of libraries of individual pure organic compounds.</jats:p>

Journal

  • Science

    Science 275 (5301), 823-826, 1997-02-07

    American Association for the Advancement of Science (AAAS)

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