Metal–Polymer Hybrid Material as a Catalyst for the Heck Coupling Reaction Under Phosphine-Free Conditions

REFERENCES

• Astruc , D. Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon–carbon coupling precatalysts: A unifying view . Inorg. Chem. 2007 , 46 , 1884 .
   PubMed Web of Science ®Google Scholar
• Zhong , L. S. ; Hu , J. S. ; Cui , Z. M. ; Wan , L. J. ; Song , W. G. In situ loading of noble metal nanoparticles on hydroxyl-group-rich titania precursor and their catalytic applications . Chem. Mater. 2007 , 19 , 4557 .
   Web of Science ®Google Scholar
• Astruc , D. ; Lu , F. ; Aranzaes , J. R. Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis . Angew. Chem., Int. Ed. 2005 , 44 , 7852 .
   PubMed Web of Science ®Google Scholar
• Moreno-Manas , E. ; Pleixats , R. Formation of carbon–carbon bonds under catalysis by transition-metal manoparticles . Acc. Chem. Res. 2003 , 36 , 638 .
   PubMed Web of Science ®Google Scholar
• Li , Y. ; Boone , E. ; El-Sayed , M. A. Size effects of PVP–Pd nanoparticles on the catalytic Suzuki reactions in aqueous solution . Langmuir 2002 , 18 , 4921 .
   Web of Science ®Google Scholar
• Herrmann , W. A. ; Brossmer , C. ; Öfele , K. ; Reisinger , C. P. ; Priermeier , T. ; Beller , M. ; Fisher , H. Palladacycles as structurally defined catalysts for the Heck olefination of chloro- and bromoarenes . Angew. Chem., Int. Ed. 1995 , 34 , 1844 .
   Web of Science ®Google Scholar
• Selvakumar , K. ; Zapf , A. ; Beller , M. New palladium carbene catalysts for the Heck reaction of aryl chlorides in ionic liquids . Org. Lett. 2002 , 4 , 3031 .
   PubMed Web of Science ®Google Scholar
• Andersson , C. M. ; Hallberg , A. Synthesis of β-arylvinyl ethers by palladium-catalyzed reaction of aroyl chlorides with vinyl ethers . J. Org. Chem. 1988 , 53 , 235 .
   Web of Science ®Google Scholar
• Köhler , K. ; Heidenreich , R. G. ; Krauter , J. G. E. ; Pietsch , J. Highly active palladium-activated carbon catalysts for Heck reactions: Correlation of activity, catalyst properties, and Pd leaching . Chem. Eur. J. 2002 , 8 , 622 .
   PubMed Web of Science ®Google Scholar
• Yang , H. ; Zhang , G. ; Hong , X. ; Zhu , Y. Dicyano-functionalized MCM-41 anchored-palladium complexes as recoverable catalysts for Heck reaction . J. Mol. Catal. A: Chem. 2004 , 210 , 143 .
   Web of Science ®Google Scholar
• Scalzullo , S. ; Mondal , K. ; Witcomb , M. ; Deshmukh , A. ; Scurrell , M. ; Mallick , K. Polymer-encapsulated metal nanoparticles: Optical, structural, micro-analytical and hydrogenation studies of a composite material . Nanotechnology 2008 , 19 , 075708 .
   PubMed Web of Science ®Google Scholar
• Palaniappan , S. ; Nivasu , V. Emulsion polymerization pathway for preparation of organically soluble polyaniline sulfate . New J. Chem. 2002 , 26 , 1490 .
   Web of Science ®Google Scholar
• Louarn , G. ; Łapkowski , M. ; Quillard , S. ; Proń , A. ; Buisson , J. P. ; Lefrant , S. Vibrational properties of polyaniline-isotope effects. J. Phys. Chem. 1996, 100, 6998.
   Web of Science ®Google Scholar
• Łapkowski , M. ; Berrada , K. ; Quillard , S. ; Louarn , G. ; Lefrant , S. ; Proń , A. Electrochemical oxidation of polyaniline in nonaqueous electrolytes: In situ Raman spectroscopic studies . Macromolecules 1995 , 28 , 1233 .
   Web of Science ®Google Scholar
• Mallick , K. ; Witcomb , M. ; Erasmus , R. ; Strydom , A. Electrical and optical properties of polyaniline with a web-like morphology . J. Appl. Poly. Sci. 2010 , 116 , 1587 .
   Web of Science ®Google Scholar
• Bera , D. ; Kuiry , S. C. ; McCutchen , M. ; Kruize , A. ; Heinrich , H. ; Meyyappan , M. ; Seal , S. In-situ synthesis of palladium nanoparticles-filled carbon nanotubes using arc-discharge in solution . Chem. Phys. Lett. 2004 , 386 , 364 .
   Web of Science ®Google Scholar
• Yao , Q. ; Kinney , E. P. ; Yang , Z. Ligand-free Heck reaction: Pd(OAc)2 as an active catalyst revisited . J. Org. Chem. 2003 , 68 , 7528 – 7531 .
   PubMed Web of Science ®Google Scholar
• Reetz , M. T. ; Westermann , E. ; Lohmer , R. ; Lohmer , G. A highly active phosphine-free catalyst system for Heck reactions of aryl bromides . Tetrahedron Lett. 1998 , 39 , 8449 – 8452 .
   Web of Science ®Google Scholar
• Gruber , A. S. ; Zim , D. Z. ; Ebeling , G. ; Monteriro , A. L. ; Dupont , J. Sulfur-containing palladacycles as catalyst precursors for the Heck reaction . Org. Lett. 2000 , 2 , 1287 – 1290 .
   PubMed Web of Science ®Google Scholar
• Gruber , A. S. ; Pozebon , D. ; Monteriro , A. L. ; Dupont , J. On the use of phosphine-free PdCl2(SEt2)2 complex as catalyst precursor for the Heck reaction . Tetrahedron Lett. 2001 , 42 , 7345 – 7348 .
   Web of Science ®Google Scholar
• Herrmann , W. A. ; Brossmer , C. ; Reisinger , C. P. ; Priermeier , T. H. ; Öfele , K. ; Beller , M. Palladacycles: Efficient new catalysts for the Heck vinylation of aryl halides . Chem. Eur. J. 1997 , 3 , 1357 – 1364 .
   Web of Science ®Google Scholar