Novel Pd-carrying composite carbon nanofibers based on polyacrylonitrile as a catalyst for Sonogashira coupling reaction

Abstract Novel Pd-carrying composite carbon nanofibers based on polyacrylonitrile were prepared by electrospinning and carbonization process. The catalytic activities of the composite nanofibers were tested with a Sonogashria coupling reaction of iodobenzene and phenylacetylene in liquid-phase. Transmission electron microscope and X-ray diffraction analyzer were used to characterize the nanofibers and the metal nanoparticles on the fibers; gas chromatograph and nuclear magnetic resonance spectroscopy were used to characterize the product of the testing reaction. The results first showed that the catalyst not only had a high catalytic activity, but also had good leaching-resistance, retrieval and reusability for the Sonogashira reaction.

[1]  Lei Wang,et al.  Application of recoverable nanosized palladium(0) catalyst in Sonogashira reaction , 2005 .

[2]  B. Erman,et al.  Palladium Nanoparticles by Electrospinning from Poly(acrylonitrile-co-acrylic acid)-PdCl2 Solutions. Relations between Preparation Conditions, Particle Size, and Catalytic Activity , 2004 .

[3]  Andreas Greiner,et al.  Nanoprocessing of polymers: applications in medicine, sensors, catalysis, photonics , 2005 .

[4]  P. Serp,et al.  Carbon nanotubes and nanofibers in catalysis , 2003 .

[5]  Chaobo Huang,et al.  Electrospun polymer nanofibres with small diameters , 2006, Nanotechnology.

[6]  D. Reneker,et al.  Growth of carbon nanostructures on carbonized electrospun nanofibers with palladium nanoparticles , 2008, Nanotechnology.

[7]  J. Strachan,et al.  Synthesis and Characterization of Tetrachlorodiarylethyne-Linked Porphyrin Dimers. Effects of Linker Architecture on Intradimer Electronic Communication. , 1998, Inorganic chemistry.

[8]  Dongho Kim,et al.  Synthesis and Excited-State Photodynamics of a Molecular Square Containing Four Mutually Coplanar Porphyrins , 1998 .

[9]  A. Szabó,et al.  Sonogashira coupling of aryl halides catalyzed by palladium on charcoal. , 2003, The Journal of organic chemistry.

[10]  M. Ihara,et al.  A concise formal total synthesis of mappicine and nothapodytine B via an intramolecular hetero Diels-Alder reaction. , 2000, The Journal of organic chemistry.

[11]  Andreas Greiner,et al.  Electrospinning: a fascinating method for the preparation of ultrathin fibers. , 2007, Angewandte Chemie.

[12]  J. G. Vries.  The Heck reaction in the production of fine chemicals , 2001 .

[13]  K. Sonogashira,et al.  Development of Pd–Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides , 2002 .

[14]  S. Kawata,et al.  Synthetic study of kedarcidin chromophore: atropselective construction of the ansamacrolide , 1999 .

[15]  Koji Nakane,et al.  Synthesis of (Z)‐3‐hexen‐1‐yl acetate by lipase immobilized in polyvinyl alcohol nanofibers , 2007 .

[16]  L. Djakovitch,et al.  Sonogashira Cross‐Coupling Reactions Catalysed by Copper‐Free Palladium Zeolites , 2004 .

[17]  Darrell H. Reneker,et al.  Carbon Nanotubes on Carbon Nanofibers: A Novel Structure Based on Electrospun Polymer Nanofibers , 2004 .

[18]  K. D. de Jong,et al.  Carbon Nanofibers: Catalytic Synthesis and Applications , 2000 .

[19]  K. Heuzé,et al.  Copper-free monomeric and dendritic palladium catalysts for the Sonogashira reaction: substituent effects, synthetic applications, and the recovery and re-use of the catalysts. , 2004, Chemistry.

[20]  C. Pham‐Huu,et al.  Carbon nanofiber supported palladium catalyst for liquid-phase reactions: An active and selective catalyst for hydrogenation of cinnamaldehyde into hydrocinnamaldehyde , 2001 .

[21]  J. Wendorff,et al.  Poly(p-xylylene) Nanotubes by Coating and Removal of Ultrathin Polymer Template Fibers , 2002 .

[22]  A. Studer,et al.  Polymer fibers as carriers for homogeneous catalysts. , 2007, Chemistry.

[23]  Jonathan S. Lindsey,et al.  Template-Directed Synthesis, Excited-State Photodynamics, and Electronic Communication in a Hexameric Wheel of Porphyrins , 1999 .

[24]  Robert D. M. Davies,et al.  Total Synthesis of the Callipeltoside Aglycon. , 2001, Angewandte Chemie.

[25]  A. Studer,et al.  Design of polymer nanofiber systems for the immobilization of homogeneous catalysts – Preparation and leaching studies , 2007 .