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

Abstract

Triphenylbismuth(V) derivatives Ph3BiX2 [X = OC6H2(NO2)3-2,4,6, OC6H2(NO2-4)Br2-2,6, OTs, OSO2C6H4OH-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.