An efficient synthesis of 2-(1-(E)-alkenyl)phenylphosphonates via Suzuki reaction of aryl nonaflates with (E)-1-alkenylboronates

•An efficient Suzuki reaction has been developed.•A series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized.•The reactions are quite general.•The reactions proceed in good yields.

An efficient and general Suzuki coupling reaction between 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters using Pd(OAc)2/PPh3 as catalysts, K2CO3 as base and DMF as solvent has been developed. This strategy allows for convenient synthesis of twelve 2-(1-(E)-alkenyl)phenylphosphonates in good to excellent yields, most of which are not readily available by the previously reported Heck reaction of the same aryl nonaflates and terminal alkenes.

Graphical abstractIn the presence of Pd(OAc)2, PPh3 and K2CO3, a series of 2-(1-(E)-alkenyl)phenylphosphonates were synthesized efficiently and stereoselectively via the Suzuki reaction of 2-phosphonylaryl nonaflates and (E)-1-alkenylboronic pinacol esters.Figure optionsDownload full-size imageDownload as PowerPoint slide