Palladium-catalyzed reaction of some triphenylbismuth(V) sulfonates and phenolates with methyl acrylate

Article abstract of DOI:10.1134/S1070363206080135

Triphenylbismuth(V) derivatives Ph₃BiX₂ [X = OC ₆H₂(NO₂)₃-2,4,6, OC ₆H₂(NO₂-4)Br₂-2,6, OTs, OSO ₂C₆H₄OH-4] react with methyl acrylate and PdCl₂ (1:3:0.04 molar ratio) in acetonitrile at 20°C to form the cross-coupling products, methyl cinnamate (0.26-0.51 mol mol^-1 starting bismuth compound) and methyl hydrocinnamate (0-0.17 mol mol ^-1); diphenyl, the homocoupling product (0-0.13 mol mol ^-1); and benzene (0.02-0.15 mol mol^-1). The reaction of Ph₃Bi(OSO₂C₆H₄OH-4)₂ is characterized by the selective formation of methyl cinnamate, but the reagent activity is low. Ph₃Bi(OTs)₂ exhibits the highest activity among the derivatives studied, but the reaction selectivity is low. The mechanisms of the palladium-catalyzed formation of homo-and cross-coupling products are proposed. Nauka/Interperiodica 2006.