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Synfacts 2006(1): 0084-0084  
DOI: 10.1055/s-2005-921699
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ligand-, Copper- and Amine-Free Sonogashira Reaction with Pd Nanoparticles

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
P. Li, L. Wang*, H. Li
Huaibei Coal Teachers College, Anhui and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

Ligand-, copper- and amine-free Sonogashira reaction was successfully achieved by use of nanoparticle palladium. The coupling reaction of o-, m- and p-substituted aryl bromides and iodides with aromatic and aliphatic terminal alkynes took place in the presence of poly(vinyl­pyrrolidone) (PVP) supported nanosized palladium metal colloids (for their preparation, see: J. S. ­Bradley, J. M. Millar, E. W. Hill J. Am. Chem. Soc. 1991, 113, 4016-4017) and potassium carbonate in ethanol to give the corresponding coupling products in 78-98% yields. The palladium catalyst was recovered by decantation and reused without significant loss of catalytic activity (90-95% yields for eight times).