Chelation-Controlled, Palladium-Catalyzed Arylation of Enol Ethers with Aryl Triflates. Ligand Control of Selection for α- or β-Arylation of ethene

Article abstract of DOI:10.1016/S0040-4020(01)80755-9

Palladium-catalyzed arylation reactions of <2-(Dimethylamino)ethoxy>ethene (1) with a series of aryl triflates were performed under a variety of reaction conditions.In particular, the influence of phosphine ligands and halide additives on regioselectivity were studied.It was found that the chelation-controlled arylation of 1 affords an expedient route for the conversion of phenols into arylacetaldehydes.Alternatively, the same starting materials could be used to synthesize acetophenones by reversing the regioselectivity with bidentate phosphine ligands.