Cucurbit[6]uril-Stabilized Palladium Nanoparticles as a Highly Active Catalyst for Chemoselective Hydrogenation of Various Reducible Groups in Aqueous Media

Abstract

Herein, we report the synthesis, characterization, and application of uniformly dispersed palladium nanoparticles supported on cucurbit[6]uril. The 2.56 wt% Pd was loaded on cucurbit[6]uril by impregnation method. Cucurbit[6]uril is a macrocyclic compound in which six glycoluril units are joined with twelve methylene bridges which not only act as support but also helped in stabilizing Pd nanoparticles. The synthesized catalyst was thoroughly characterized by various physicochemical methods. The high resolution transmission electron microscopic analysis revealed the uniform distribution of Pd nanoparticles with average size of ∼3 nm over the cucurbit[6]uril surface. Furthermore, the synthesized catalyst was used for the chemoselective hydrogenation of various reducible (epoxide, olefin, carbonyls, nitrile, azo, imines and nitroarenes) groups with excellent conversion, selectivity (> 99%) and high turnover frequency (up to 2,05,882 h) in aqueous and in some cases with water-THF mixture. Also, the catalyst was successfully recycled several times (>10 times) without losing any significant conversion and selectivity. Moreover, the leaching results were confirmed by analyzing reaction mixture by inductively coupled plasma atomic emission spectroscopy. Furthermore, the kinetic studies reveal the reaction rate depends on substrate concentration. The reaction mechanism was investigated by studying the reaction through drift FTIR studies.