Silica-bound poly-4-oxa-6,7-bis(diphenylarsino)heptylsiloxane palladium(0) complex catalyzed Heck arylation of butyl acrylate and acrylamide with aryl halides

A silica-bound poly-4-oxa-6,7-bis(diphenylarsino)heptylsiloxane palladium(0) complex has been synthesized by treatment of poly-4-oxa-6,7-dichloroheptylsiloxane with potassium diphenylarsenide in THF and palladium chloride in acetone, followed by the reduction with hydrazine hydrate in ethanol. It was found that the title complex is an efficient catalyst for the Heck arylation reaction of butyl acrylate and acrylamide with aryl halides. This polymeric palladium(0) catalyst is stable and can be reused without noticeable loss of activity. Hence this paper presents a simple and practical procedure for the stereoselective synthesis of a variety of (E)-butyl cinnamates and (E)-cinnamamides.