Semi-continuous nanofiltration-coupled Heck reactions as a new approach to improve productivity of homogeneous catalysts

Abstract Substantial increase in homogeneous catalyst productivity for a well known Heck coupling was achieved by nanofiltration-coupled catalysis. The use of nanofiltration membranes enabled catalyst separation and allowed subsequent catalyst recycle and reuse. This new technique demonstrated potential for general applicability to homogeneously catalysed organic syntheses.

[1]  W. Herrmann,et al.  Chelating N-heterocyclic carbene ligands in palladium-catalyzed heck-type reactions 1 N-Heterocyclic , 1998 .

[2]  K. R. Seddon,et al.  The Heck reaction in ionic liquids: A multiphasic catalyst system , 1999 .

[3]  S. Akutagawa.  Asymmetric synthesis by metal BINAP catalysts , 1995 .

[4]  Udo Kragl,et al.  Polymer enlarged oxazaborolidines in a membrane reactor: enhancing effectivity by retention of the homogeneous catalyst , 1998 .

[5]  M. Shirai,et al.  Comparison of activity and selectivity of various metal-TPPTS complex catalysts in ethylene glycol toluene biphasic Heck vinylation reactions of iodobenzene , 1998 .

[6]  S. Sartori,et al.  DRAMATIC INCREASE OF TURNOVER NUMBERS IN PALLADIUM-CATALYZED COUPLING REACTIONS USING HIGH-PRESSURE CONDITIONS , 1996 .

[7]  G. Crisp.  Variations on a theme—recent developments on the mechanism of the Heck reaction and their implications for synthesis , 1998 .

[8]  M. Shirai,et al.  Heck reactions using water-soluble metal complexes in supercritical carbon dioxide , 1999 .

[9]  R. Heck.  Palladium reagents in organic syntheses , 1985 .

[10]  T. Jeffery.  Tetraalkylammonium salt-based catalyst systems for directing Heck-type reactions. Arylation of allyltrimethylsilane , 2000 .

[11]  M. Reetz,et al.  A New Catalyst System for the Heck Reaction of Unreactive Aryl Halides. , 1998, Angewandte Chemie.

[12]  T. Sugihara,et al.  Effects of high pressure on the heck reaction. Is it possible to control dehydropalladation of alkylpalladium intermediates having β-hydrogens? , 1995 .

[13]  R. Heck.  Palladium‐Catalyzed Vinylation of Organic Halides , 2005 .

[14]  I. Beletskaya,et al.  The heck reaction as a sharpening stone of palladium catalysis. , 2000, Chemical reviews.

[15]  Lloyd S. White,et al.  Solvent recovery from lube oil filtrates with a polyimide membrane , 2000 .

[16]  M. Beller,et al.  Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro- and Bromoarenes†‡ , 1995 .

[17]  A. Hallberg,et al.  Microwave-Promoted Palladium-Catalyzed Coupling Reactions , 1996 .

[18]  M. Deshpande,et al.  Heck reactions in solid phase synthesis , 1994 .

[19]  L. U. Gron,et al.  Tailoring aqueous solvents for organic reactions: Heck coupling reactions in high temperature water , 1999 .

[20]  W. Herrmann,et al.  Dicationic chelating N-heterocyclic carbene complexes of palladium: new catalysts for the copolymerisation of C2H4 and CO , 1999 .

[21]  Manfred T. Reetz,et al.  Allylic Substitution with Dendritic Palladium Catalysts in a Continuously Operating Membrane Reactor , 1999 .

[22]  M. Reetz,et al.  A highly active phosphine-free catalyst system for Heck reactions of aryl bromides , 1998 .

[23]  K. Sharpless,et al.  Coelacanths and catalysis , 1994 .

[24]  W. Herrmann,et al.  HOMOLEPTIC CHELATING N-HETEROCYCLIC CARBENE COMPLEXES OF PALLADIUM AND NICKEL , 1999 .

[25]  W. Herrmann,et al.  Metal Complexes of N‐Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis , 1995 .

[26]  A. Spencer.  A highly efficient version of the palladium-catalysed arylation of alkenes with aryl bromides , 1983 .

[27]  L. Hegedus.  Transition Metals in the Synthesis of Complex Organic Molecules , 1993 .