Arylation and Vinylation Reactions of Benzo[b]furan via Organopalladium Intermediates

The Heck reaction of benzo[b]furan with arylpalladium chloride leads to the formation of 2-arylbenzo[b]-furan derivatives. In the presence of palladium acetate, benzo[b]furan reacts in benzene to give 2,2′-bibenzo[b]furyl, accompanied by 2-arylbenzo[b]furan. In the phenylation of [2-2H]benzo[b]furan with phenylpalladium salts, it was confirmed that no hydride shift takes place in the reaction. In the presence of palladium acetate, benzo[b]furan also reacts with olefin to produce benzo[b]furyl-substituted olefins, accompanied by a small amount of 2,2′-bibenzo[b]furyl, and from the reaction of [β,β-2H2]styrene and benzo[b]furan in the presence of palladium acetate it was confirmed that no hydride shift occurs in the reaction.