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Synlett 2013; 24(2): 254-258
DOI: 10.1055/s-0032-1317963
letter
© Georg Thieme Verlag Stuttgart · New York

The [RPPh3]2[Pd2X6] as a Catalyst Precursor for the Heck Cross-Coupling Reaction by in situ Formation of Stabilized Pd(0) Nanoparticles

Abdol Reza Hajipour*
a   Department of Pharmacology, University of Wisconsin Medical School, 1300 University Avenue, Madison, WI 53706-1532, USA
b   Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran   Fax: +98(311)3912350   Email: haji@cc.iut.ac.ir
,
Ghobad Azizi
b   Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran   Fax: +98(311)3912350   Email: haji@cc.iut.ac.ir
› Author Affiliations
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Publication History

Received: 10 November 2012

Accepted after revision: 10 December 2012

Publication Date:
08 January 2013 (online)

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Abstract

Pd(II) anionic, square planar complexes of the type [RPPh3]2[Pd2X2Cl4], where X = Cl, Br, have been applied for the first time as a catalyst precursor for the Heck reaction carried out in DMF at 140 °C. The highest yield was obtained for the most reducible ones, [MePPh3]2[Pd2Br2Cl4], in DMF in the presence of NaHCO3 as a base. It was found that during the reaction, phosphonium halide stabilized Pd(0) nanoparticles of about 10 nm, which have been formed in situ from the palladium(II) precursor and Pd(0) colloidal nanoparticles acts as the reservoir for Pd(II) species via activation of the metal surface through the oxidative addition of aryl halides.

Key words

olefination - arylation - catalysis - palladium - nano­structures

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  • References and Notes

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