Journal
ADVANCED FUNCTIONAL MATERIALS
Volume 21, Issue 6, Pages 1064-1075Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adfm.201001912
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Funding
- Region Bourgogne
- CNRS
- University of Burgundy
- Russian Foundation for Basic Research [09-03-01172a]
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Pd@PPy hybrid catalytic materials are synthesized in water via redox polymerization reaction of pyrrole with [Pd(NH3)(4)Cl-2]. The nanocomposites formed are composed of highly dispersed palladium particles which are either zerovalent or easily reducible, and are embedded in spherical polypyrrole globules. A unique combination of high palladium dispersion (NP size: 2.4 nm) and elevated palladium content (35 wt%) is obtained. The components of these novel nanocomposites are characterized by means of FTIR, XPS, XRD, SEM, and TEM microscopy techniques. The process of formation in solution is also monitored using UV-visible and DLS techniques. The application of these novel hybrid nanomaterials in the palladium-catalyzed direct arylation of heteroaromatics is reported. High efficiency in C-C bond formation is obtained using these materials. Furans and thiophenes are arylated by using bromoarenes. Pd@PPy nanocomposites can efficiently couple n-butyl furan and n-butyl thiophene with bromobenzene and bromoquinoline, as well as with activated or deactivated electron-poor and electron-rich functionalized bromoarenes. Thus, a clean reaction process is developed that combines the absence of organic ligand in catalytic reactions and easy recovery of Pd@PPy nanocomposite via simple filtration. Preliminary kinetic and post-catalysis studies suggest a molecular or colloidal soluble active species. These very active species are efficiently delivered by the nanocomposites and susceptible to a surprisingly uniform back redeposition within the polypyrrole support.
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