Phenyl Derivatives of Antimony(III, V) and Bismuth(III, V) in the Presence of Palladium Salts, as C-Phenylating Agents for Methyl Acrylate

The C-phenylation of methyl acrylate to methyl cynnamate with Ph3Sb, Ph3SbX2 (X = Cl, OAc), Ph3Bi, and Ph3BiX2 (X = OAc, O2CEt) in the presence of PdCl2, Pd(OAc)2, Li2PdCl4, NaPd(OAc)Cl2, and Na2Pd(OAc)2Cl2 was studied to show that the reactions with Ph3Sb and Ph3Sb(OAc)2 are more selective and give higher yields of the target product than those with Ph3Bi and Ph3Bi(OAc)2, while Ph3M(OAc)2 are preferred over Ph3M. Copper(II) alkanecarboxylate additives have no effect on the yield of methyl cynnamate in the reactions with Ph3Sb.