Surfactant assisted Pd/C catalyzed Sonogashira reaction in aqueous media

The Sonogashira reaction of iodobenzene with phenylacetylene was carried out in water using Pd/C as catalyst and surfactants as additives. The effect of various cationic and anionic surfactants on the activity of Pd/C for the above reaction was studied. The reaction was found to be promoted by cationic surfactants only. The effect of surfactant concentration, different types of bases and temperature on conversion is reported. Our results are comparable with previously reported results on alternative media for Sonogashira reaction involving Pd/C. Our protocol eliminates the need of copper (I) salt, ligand and inert atmosphere which are essential in conventional methods. A reasonable mechanism for mass transfer and catalysis of the reaction is proposed. (C) 2011 Elsevier B.V. All rights reserved.