Palladium-catalyzed cross-coupling of aryl chlorides with alkenylboronic acids with low E/Z isomerization

Using a bulky electron-rich monodentate benzoferrocenyl phosphine as supporting ligand, an efficient protocol for stereoselective palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides with alkenylboronic acids was uncovered. Using this protocol, both trans- and cis-alkenylboronic acids can be coupled with high stereoselectivity giving the corresponding vinylarenes in good to quantitative yields. Electron-poor and -rich aryl chlorides including highly hindered ones are all suitable substrates for the reaction.