Surfactant-Assisted Aqueous-Phase Heck Reaction

Abstract

The Heck reaction of iodobenzene with styrene was carried out using aqueous surfactant solution as reaction media. The effect of various cationic and anionic surfactants on the activity of Pd/C in water for the Heck reaction was studied. The reaction is found to be catalyzed only by cationic surfactants. The effect of surfactant concentration, different bases, reaction time, and temperature on conversion is reported. The results have been compared with the results of previously reported alternative media for the Heck reaction using Pd/C. A reasonable mechanism for the Heck reaction based on adsorption of surfactant on the surface of catalyst is proposed.

Keywords:

• Heck reaction
• Pd/C
• surfactants
• water

Notes

Reaction conditions: Substrate: 0.33 mol iodobenzene/kg of water; styrene: 1.2 mol/mol of iodobenzene; K₂CO₃: 1.5 mol/ mol of iodobenzene; surfactant: 0.5 mol/mol of iodobenzene; Pd/C: 0.01 mol/mol of iodobenzene; temperature: 353 K; time of reaction: 4 hours.

Reaction conditions: substrate: 0.33 mol iodobenzene/kg of water; styrene: 1.2 mol/mol of iodobenzene; Base:1.5 mol/mol of iodobenzene; surfactant: 0.5 mol/mol of iodobenzene; Pd/C: 0.01 mol/mol of iodobenzene; temperature: 353 K; time of reaction: 4 hours.

Reaction conditions: substrate: 0.33 mol iodobenzene/kg of water; Olefin: 1.2 mol/mol of iodobenzene; K ^₂ CO ^₃ :1.5 mol/mol of iodobenzene; surfactant: 0.5 mol/ mol of iodobenzene; Pd/C: 0.01 mol/mol of iodobenzene; temperature: 353 K; time of reaction: 4 hours.