THE PALLADIUM-CATALYSED ARYLATION OF ACTIVATED ALKENES WITH AROYL CHLORIDES

Article abstract of DOI:10.1016/S0022-328X(00)82707-2

Aroyl chlorides react with activated alkenes in presence of a tertiary amine and a catalytic amount of palladium acetate to give arylated alkenes, specifically cinnamic acid derivatives and stilbenes.The reaction involves a highly efficient decarbonylation of the aroyl chloride.High yields can be obtained at low catalyst concentration by choice of an appropriate base.The reaction is not particularly sensitive to substituents in the aroyl chloride, although strongly electron-donating groups are advantagenous (yields up to 98percent).With monosubstituted alkenes E-isomers are formed with almost complete specificity.A mechanism for the reaction is proposed.