Synthesis of diethyl 2-(aryl)vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes

Pd-catalysed procedures for the direct Heck arylation of diethyl vinylphosphonate with various aryl or heteroaryl halides toward the synthesis of diethyl 2-(aryl)vinylphosphonates are reported. Several homogeneous catalytic systems (i.e. Herrmann palladacycle, Nolan (NHC)-palladium catalyst, Pd(OAc)2/PPh3) were used and compared within the study. High conversions and selectivities were achieved under optimised conditions (2 mol% [Pd], NMP, K2CO3, 140 °C) whatever the homogeneous catalyst used.

Graphical abstractThe Pd-catalysed synthesis of diethyl 2-(aryl)vinylphosphonates by direct Heck arylation of diethyl vinylphosphonate with various aryl or heteroaryl halides is reported. Several homogeneous catalytic systems were used and compared giving high conversions and selectivities under optimised conditions.Figure optionsDownload full-size imageDownload as PowerPoint slide