Palladium-Catalyzed Cross-Carbonylation of Aryl Iodides with Five-Membered Cyclic Olefins

Article abstract of DOI:10.1021/jo00127a035

Intermolecular cross-carbonylation of aryl iodides with five-membered cyclic olefins such as dihydrofurans and cyclopentene was found to proceed by using a catalyst system of PdCl2/PPh3 under CO (3-5 atm) in the presence of a tertiary amine.With 2,3- and 2,5-dihydrofurans, 2-aroyl-4,5-dihydro- and 3-aroyl-2,3-dihydrofurans were obtained as the predominant products, respectively, while the reaction of iodobenzene with cyclopentene gave a mixture of three regioisomers of benzoylcyclopentene.The yields of the products were observed to be markedly influenced by the amount of triphenylphosphine added.