Fluorous phase separation techniques in catalysis

Fluorous solvents have limited miscibility with conventional organic solvents. Combined with the fact that compounds functionalized with perfluorinated groups often dissolve preferentially in fluorous solvents this can be used to extract fluorous components from reaction mixtures. This review discusses the application and potential of fluorous phase separation techniques for the recovery of soluble metal catalysts.

[1]  Dennis P Curran,et al.  Strategy-Level Separations in Organic Synthesis: From Planning to Practice. , 1998, Angewandte Chemie.

[2]  Gabor Kiss,et al.  Molecular Engineering in Homogeneous Catalysis: One-Phase Catalysis Coupled with Biphase Catalyst Separation. The Fluorous-Soluble HRh(CO){P[CH2CH2(CF2)5CF3]3}3 Hydroformylation System , 1998 .

[3]  G. Koten,et al.  Ortho-bis(amino)arylnickel(II) halide complexes containing perfluoroalkyl chains as model catalyst precursors for use in fluorous biphase systems , 1998 .

[4]  J. Gladysz,et al.  Organometallic reactivity patterns in fluorocarbons and implications for catalysis: Synthesis, structure, solubility, and oxidative additions of a fluorous analogue of Vaska's complex, trans-Ir(CO)(Cl)[P(CH2CH2(CF2) 5CF3)3]2 , 1998 .

[5]  P. Knochel,et al.  PALLADIUM-CATALYZED CROSS-COUPLING OF ORGANOZINC BROMIDES WITH ARYL IODIDES IN PERFLUORINATED SOLVENTS , 1997 .

[6]  Vittal K. Yachandra,et al.  Fluorous Biphasic Catalysis: Complexation of 1,4,7‐[C8F17(CH2)3]3‐1,4,7‐Triazacyclononane with [M(C8F17(CH2)2CO2)2] (M = Mn, Co) To Provide Perfluoroheptane‐Soluble Catalysts for Alkane and Alkene Functionalization in the Presence of t‐BuOOH and O2 , 1997 .

[7]  R. Mülhaupt,et al.  Carbosilane Dendrimers with Perfluoroalkyl End Groups. Core−Shell Macromolecules with Generation-Dependent Order , 1997 .

[8]  S. Quici,et al.  Metal Complexes of a Tetraazacyclotetradecane Bearing Highly Fluorinated Tails: New Catalysts for the Oxidation of Hydrocarbons under Fluorous Biphasic Conditions , 1997 .

[9]  Matthias Schuster,et al.  Olefin Metathesis in Organic Chemistry , 1997 .

[10]  W. Leitner,et al.  Perfluoroalkyl‐Substituted Arylphosphanes as Ligands for Homogenous Catalysis in Supercritical Carbon Dioxide , 1997 .

[11]  J. Gladysz,et al.  Transition metal catalysis in fluorous media: Practical application of a new immobilization principle to rhodium-catalyzed hydroboration , 1997 .

[12]  P. Knochel,et al.  Transition Metal Catalyzed Oxidations in Perfluorinated Solvents , 1997 .

[13]  M. Therien,et al.  Synthesis, structure, electronic spectroscopy, photophysics, electrochemistry, and X-ray photoelectron spectroscopy of highly-electron-deficient [5,10,15,20-tetrakis(perfluoroalkyl)porphinato]zinc(II ) complexes and their free base derivatives , 1996 .

[14]  T. Umemoto.  Electrophilic Perfluoroalkylating Agents. , 1996, Chemical reviews.

[15]  R. Hughes,et al.  Selective Solubility of Organometallic Complexes in Saturated Fluorocarbons. Synthesis of Cyclopentadienyl Ligands with Fluorinated Ponytails , 1996 .

[16]  Brian Evans,et al.  FTIR and AFM Studies of the Kinetics and Self-Assembly of Alkyltrichlorosilanes and (Perfluoroalkyl)trichlorosilanes onto Glass and Silicon , 1995 .

[17]  P. L. Nostro.  Phase separation properties of fluorocarbons, hydrocarbons and their copolymers , 1995 .

[18]  D. M. Grove,et al.  Homogeneous catalysts based on silane dendrimers functionalized with arylnickel(II) complexes , 1994, Nature.

[19]  I. Horváth,et al.  Facile catalyst separation without water: fluorous biphase hydroformylation of olefins. , 1994, Science.

[20]  B. Hanson,et al.  Two-Phase Hydroformylation of Octene-1 with Rhodium Complexes of P[C6H4(CH2)mC6H4-p-SO3Na]3 (m = 3, 6). Rate and Selectivity Enhancement with Surface-Active Phosphines , 1994 .

[21]  W. Herrmann,et al.  Water‐Soluble Ligands, Metal Complexes, and Catalysts: Synergism of Homogeneous and Heterogeneous Catalysis , 1993 .

[22]  T. A. Brown,et al.  Micelles and aggregates of fluorinated surfactants , 1991 .

[23]  Paul S. Smith,et al.  Dissolution of poly(tetrafluoroethylene) , 1985 .

[24]  J. G. Riess,et al.  Solubility and transport phenomena in perfluorochemicals relevant to blood substitution and other biomedical applications , 1982 .

[25]  T. Maugh.  Blood substitute passes its first test. , 1979, Science.

[26]  W. Zisman,et al.  Spreading of liquid perfluorinated hydrocarbons on water , 1972 .

[27]  James E. Huheey,et al.  The Electronegativity of Groups , 1965 .

[28]  R. Scott.  The Anomalous Behavior of Fluorocarbon Solutions , 1958 .