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Palladium Catalyzed Carbonylative Vinylation of Aryl Halides with Olefins and Carbon Monoxide

  • Kim, Jin-Il (Department of industrial Chemistry, Hanyang University) ;
  • Ryu, Cheol-Mo (Department of Chemical Engineering, Kyonggi National Open University)
  • Published : 1987.08.20

Abstract

The reaction of aryl iodides or bromides with olefins in the presence of 1 mol % of $PdCl_2(PPh_3)_2$ and 3 equiv. of $n-Bu_3N\; at\; 100^{\circ}C$ in carbon monoxide atmosphere gave the corresponding aryl vinyl ketones in good yields with small amount of vinylated 1-aryl olefins. But, when the reaction was proceeded under the 10 atm of carbon monoxide, aryl vinyl ${\alpha}$-diketones and aryl vinyl ketones were obtained in moderate to good yields. The reaction was tolerant of a wide variety of functional groups on either the aryl halides or olefin compounds. Reactivity of aryl halide decrease in the order; aryl iodide > aryl bromide ${\gg}$aryl chloride. In general, the reaction proceeded well and gave good yields of aryl vinyl ketones and aryl vinyl ${\alpha}$-diketones when reactants are substituted with electron withdrawing groups.

Keywords

References

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Cited by

  1. ChemInform Abstract: Palladium Catalyzed Carbonylative Vinylation of Aryl Halides with Olefins and Carbon Monoxide. vol.19, pp.8, 1987, https://doi.org/10.1002/chin.198808118
  2. Palladium-Catalyzed Double and Single Carbonylation of Aryl Halides and Allylic Compounds vol.68, pp.2, 1987, https://doi.org/10.1246/bcsj.68.433