Palladium-EDTA and palladium-EdteH_4 catalyzed Heck coupling reactions in pure water

Palladium-catalyzed Heck coupling reactions of styrene with bromoarene derivatives are carried out under aerobic conditions in water using water-soluble N,N,N ,N -tetrakis(2-hydroxyethyl)ethylenediamine (EdteH_4) and ethylenediaminetetraacetic acid disodium salt (Na_2EDTA) as ligands. The effect of different bases, catalyst loading, and additives is also monitored. The olefination of bromoarenes with styrene affords the desired products in high yields. The Na_2PdCl_4-Na_2EDTA precatalyst system is also used for the preparative scale (50.0 mmol) synthesis of 4-acetyl-trans-stilbene and 4-styrylbenzaldehyde without a noticeable decrease in the activity. Recycling studies on the Na_2PdCl_4 - Na_2EDTA precatalyst system are also tested in the coupling of 4-bromoacetophenone with styrene.