Gold Nanoparticles Supported on Poly(Phenylene Oxide) as Selective and Versatile Catalyst for Hydroamination of Arylacetylenes with Anilines

Abstract

Heterogeneous catalysts based on gold nanoparticles supported on organic polymers are emerging as promising systems, owing to their efficiency, selectivity, recyclability, and compatibility with industrial and pharmaceutical standards. In this work, the catalytic performance of gold nanoparticles supported on poly(2,6-dimethyl-1,4-phenylene oxide) in the hydroamination reaction between aniline and phenylacetylene is reported by varying the reaction conditions. Furthermore, different combinations of phenylacetylene with substituted anilines were investigated, showing that the introduction of electron-withdrawing groups on the aniline aromatic ring leads to higher conversions while maintaining high selectivity toward the formation of E-configured imines, likely due to the enhanced acidity of the ammonium intermediate involved in the rate-determining proton-transfer step.