Reaction of aryl halides with (Z)-1-ethoxy-2-tributylstannylethene: A versatile method for the introduction of 2-ethoxyethenyl group into aromatic nuclei

The reaction of 4-substituted bromobenzenes, except for 4-bromophenol and 4-bromoaniline, with (Z)-1-ethoxy-2-tributylstannylethene is well prompted by the catalytic action of dichlorobis(triphenylphosphine)palladium in dimethylformamide in the presence of tetraethylammonium chloride to give (Z)-1-ethoxy-2-(4-substituted phenyl)ethene. The method is also useful for the introduction of a 2-ethoxyethenyl moiety into heteroaromatic rings such as pyridine, thiophene, indole.