Nano–silica functionalized with thiol–based dendrimer as a host for gold nanoparticles: An efficient and reusable catalyst for chemoselective oxidation of alcohols

Abstract

In this paper, we present the synthesis of Au nanoparticles supported on nanosilica thiol based dendrimer, nSTDP. The catalyst was prepared by reduction of HAuCl4 with NaBH4 in the presence of nSTDP. The resulting Aunp–nSTDP materials were characterized by FT–IR and UV–vis spectroscopic methods, SEM, TEM, TGA, XPS and ICP analyses. The characterization of the catalyst showed that Au nanoparticles with the size of 2–6 nm are homogeneously distributed on the nSTDP dendrimer with a catalyst loading of about 0.19 mmol/g of catalyst. The Aunp–nSTDP catalyst was used in the oxidation of alcohols with tert–butyl hydroperoxide (TBHP) as oxidant. The influence of vital reaction parameters such as solvent, oxidant and amount of catalyst on the oxidation of alcohols was investigated. These reactions were best performed in an acetonitrile/water mixture (3:2) in the presence of 0.76 mol% of the catalyst on the basis of the Au content at 80 °C under atmospheric pressure of air to afford the desired products in high yields (80–93% for benzyl alcohols). The Aunp–nSTDP catalyst exhibited a high selectivity toward the corresponding aldehyde and ketone (up to 100%). Reusabiliy and stability tests demonstrated that the Aunp–nSTDP catalyst can be recycled with a negligible loss of its activity. Also this catalytic exhibited a good chemoselectivity in the oxidation of alcohols.