Copper Dithiol Complex Supported on Silica Nanoparticles: A Sustainable, Efficient, and Eco-friendly Catalyst for Multicomponent Click Reaction

Abstract

Silica-nanoparticle-supported copper-containing ionic liquid (SNIL-Cu­(II)) provided a highly stable, active, reusable, spherical, and solid-phase catalyst for click chemistry. The SNIL-Cu­(II) catalyst was readily prepared from 1,2-bis(4-pyridylthio)­ethane immobilized on silica nanoparticles modified with 3-chloropropyltrimethoxysilane and Cu­(OTf)2, and the morphology, structure, and properties of nanoparticles were investigated through different analytical tools. This catalytic system showed high activity in a one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles by click reactions between a variety of alkynes, organic halides, and sodium azide at room temperature in aqueous polyethylene glycol as a green medium with a high turnover frequency (up to 7920 h–1). Moreover, the SNIL-Cu­(II) was also used as an efficient catalyst for the preparation of a series of multifold 1,4-disubstituted 1,2,3-triazoles. Also, this unique catalyst was readily reused without any decrease in its catalytic activity to give the corresponding triazoles quantitatively.

Catalytic Assessment of Copper(I) Complexes and a Polymer Analog towards the One‐Pot Synthesis of Imines and Quinoxalines

“…Hence we were interested in developing a stable non‐noble metal catalyst for the one‐pot synthesis of imines without utilizing harsh conditions. Copper is one of the abundant and cheap metals known and the activity of copper complexes are well envisioned from the literature reports, and it is well comparable to the activity of platinum group complexes in various catalytic applications …”

Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system

“…As shown in Figure 3, the weight loss of nanoparticles between 30°C and 750°C was observed by TG and DTG curves. For nano-SiO 2 (NS), γ-chloropropyl-functionalized nano-SiO 2 particles (NS-Cl) and nano-SiO 2 immobilized DMAP derivative (NS-DMAP), the weight loss from 30 to 200°C was attributed to the desorption of physically absorbed water [25], which could be confirmed by the peak of DTG at 30 to 200°C. And another main weight loss was observed at 400°C to 600°C, which was ascribed to the decomposition of coupled CPTMS.…”

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

“…Silica gel decorated with a sulfur-containing ligand was developed by Tavassoli et al as a new support material for Cu(I/II) [182]. In situ reduction with sodium ascorbate of the complex obtained by stirring the modified silica with CuCl 2 or Cu(OTf) 2 afforded the corresponding CuAAC catalyst 42 .…”