Abstract
The palladium-catalyzed three-component coupling reaction of acetylenes, aryl halides, and hydride and it’s application to polymer synthesis are described. The coupling reaction of 1,2-diphenylacetylene, iodobenzene, and sodium diethyl benzylmalonate was carried out at 80°C for 48 h in 1,4-dioxane with Pd(OAc)2 / tri-o-tolylphosphine, from which triphenylethylene was obtained in 71% isolated yield. The benzylic hydrogen of sodium diethyl benzylmalonate was supposed to be a hydride source in the present reaction by detecting diethyl benzalmalonate in the reaction system. Based on the results, the coupling polymerization of l,2-bis(4-phenylethynylphenyl) ethane, 4,4′-diiodobiphenyl, and sodium diethyl benzylmalonate was carried out at 80°C for 48 h to produce a polymer (Mn= 8500, Mw / Mn = 3.0) in high yield. Using various aryl dihalides, the corresponding polymers having trisubstituted ethylene units were also obtained in high yields.
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