Energy-Efficient Green Catalysis: Supported Gold Nanoparticle-Catalyzed Aminolysis of Esters with Inert Tertiary Amines by C–O and C–N Bond Activations

Abstract

Catalyzed by supported gold nanoparticles, an aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of tertiary amides. Comparison studies indicated that the gold nanoparticles could perform energy-efficient green catalysis at room temperature, whereas Pd(OAc)2 could not.

Gold nanoparticles in aqueous solutions: influence of size and pH on hydrogen dissociative adsorption and Au(iii) ion reduction

“…The minus sign indicates that the addition of electrons to a particle decreases its potential, so that the constant k is positive. Comparison of eqn (3) and (4) shows that the greater the shift of the LSPR band, the lower the nanoparticle potential. Formula (4) can be substantiated as follows.…”

“…Bulk gold is a chemically inert metal exhibiting no catalytic activity, while nanosized gold (up to 5 nm) deposited on various substrates catalyzes a variety of reactions of organic synthesis. [1][2][3][4] The gold hydrosol shows intensive absorption in the visible region caused by collective excitation of the conduction electrons by light. The optical properties of the hydrosol depend substantially on the size of nanoparticles, density of electrons in them and properties of the dispersion medium and interface.…”

Chlorinated 2‐hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties

“…Compound 5 was functionalized by amide coupling and esterification . The reaction between oxazolinic acid 5 and the 6‐aminobenzothiazole led to the product 6 a in 62 % yield (Table , entry 1).…”

Organic Synthesis Catalyzed by Supported Gold Nanoparticles

“…A schematic illustration of the reaction mechanism was given by Friend et al (Scheme 16). 154 Subsequently, Bao and coworkers stated that gold nanoparticles could catalyze cross-coupling of tertiary amine and esters for the selective synthesis of tertiary amides, which gave moderate to excellent yields even at 25 C. 155 By comparison, the homogeneous catalyst Pd(OAc) 2 was not active under identical reaction conditions. In this work, the authors proposed a reaction pathway different from that of the oxidative cross-coupling of aldehydes with secondary amines (Scheme 17).…”