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Synfacts 2010(4): 0498-0498  
DOI: 10.1055/s-0029-1219468
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Free Sonogashira Coupling in Water with a PS-PEG Palladium Complex

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
T. Suzuka*, Y. Okada, K. Ooshiro, Y. Uozumi*
Institute for Molecular Science, Okazaki and University of the Ryukyus, Nishihara, Japan
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

An amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported palladium phosphine complex was applied to the Sonogashira coupling of aryl halides with terminal alkynes in water. Thus, the PS-PEG palladium complex 1 was prepared from PS-PEG-NH2, diphenylphosphinobenzoic acid, and [PdCl(π-C3H5)]2 according to the reported procedures (Tetrahedron Lett. 1997, 38, 3557). The Sonogashira coupling of iodobenzene 2 with phenyl­acetylene 3 was performed with 5 mol% palladium of the polymeric catalyst 1 in water to give the diphenylacetylene 4 in 99% yield.