Three-Component Coupling Polymerization of Bisallene, Aryl Dihalide, and Nucleophiles via π-Allylpalladium Complex
Citations Over TimeTop 14% of 1996 papers
Abstract
A novel palladium(0)-catalyzed three-component coupling polymerization of a bisallene (1,2,10,11-dodecatetraene, 1), aryl dihalides (2a−e), and a nucleophile (sodium diethyl malonate, 3) is described. By the reaction of 1, 4,4‘-diiodobiphenyl (2a), and 3 in the presence of a palladium catalyst in 1,4-dioxane at 80 °C for 2 days, a polymer (4a) was obtained in high yield (97%, M̄n = 11 100). The structure of the resulting polymer (4a) was confirmed by 13C-, 1H-NMR, and IR spectra, from which the double bonds in the polymer backbone were detected quantitatively and were found to be mainly composed of E-isomer. The concentration of the palladium catalyst was found to affect the degree of polymerization. By using some aryl dihalides (2b−e), the corresponding polymers were also obtained in high yield.
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