Metal–Polymer Hybrid Material as a Catalyst for the Heck Coupling Reaction Under Phosphine-Free Conditions

Abstract

A method is described for making a poly-aminophenol-based hybrid material by in situ polymerization of aminophenol using palladium acetate as the oxidant. The oxidative polymerization of aminophenol leads to the formation of poly-aminophenol, while the reduction of palladium acetate results in the formation of palladium nanoparticles. The palladium nanoparticles were found to be highly dispersed and stabilized throughout the polymer matrix. The hybrid nanocomposite material showed excellent catalytic efficiency with respect to a Heck coupling reaction at a relatively low temperature and under flexible conditions.

Keywords:

• Carbon–carbon coupling reaction
• IPCF
• metal–polymer composite
• palladium nanoparticle
• TEM

Notes

Notes. Reagents and reaction conditions: Aryl iodides (1.0 mmol), alkenes (1.5 mmol), triethyl amine (1.5 mmol), DMF (5 ml), and catalyst [Pd–poly-(o-aminophenol)] (4 mg), for 8 h at 80 °C.

Notes. Reagents and reaction conditions: Aryl bromides (1.0 mmol), alkenes (1.5 mmol), triethyl amine (1.5 mmol), DMF (5 ml), and catalyst [Pd–poly-(o-aminophenol)] (4 mg), for 8 h at 80 °C.

Notes. Dimethylformamide (DMF), dimethylacetamide (DMA), and N-methylpyrrolidone (NMP).