A Coupling Reaction of Acid Chlorides with Alkynes Using a PS-Pd Complex

Significance

A diphenylphosphinoethane(dppe)-functionalized polystyrene resin supported palladium(0) complex [PS-dpp-Pd(0)] was applied to the coupling reaction of acid chlorides with terminal alkynes under aerobic conditions. Thus, the PS-dpp-Pd(0) was prepared from dppe, chloromethylpolystyrene, and [PdCl₂(PhCN)₂] according to the reported procedures (Tetrahedron Lett. 2009, 50, 6418). The coupling reaction of the p-chloro­benzoyl chloride (2) with ethynylbenzene (3) was performed with 0.5 mol% palladium of the polymeric catalyst 1 under aerobic conditions to give the 1-(4-chlorophenyl)-3-phenylpropynone (4) in 98% yield. This catalyst was recovered and reused five times without any loss of catalytic activity.