Examination of Ligand Effects in the Heck Arylation Reaction

The Heck arylation reaction between aryl bromide and iodide with methyl acrylate was evaluated. A new class of ligands, R–N(CH2CH2PPh2)2, is compared with conventional monodentate and bidentate ligands, and was found to confer greater catalyst stability. The nitrogen substituent (R) has a noticeable effect on the rate of the turnover. We believe this is the first report of the application of such hemilabile ligands in Heck arylation chemistry.