CuSO₄ nanoparticles loaded onto poly (toluenesulfonic acid‐formaldehyde)/polyethyleneimine composites: An efficient retrievable catalyst for A₃/decarboxylative A₃ reactions

Abstract

Using polymeric composite incorporated transition metal nanoparticles to promote various organic reactions has been found as one of the most powerful strategies in organic synthesis. In this paper, CuSO4 nanoparticles (CuSO4 NPs) anchored on the surface of polymeric composites comprising of water‐insoluble acidic poly (toluenesulfonic acid‐formaldehyde) (PTSAF) and water‐soluble basic polyethyleneimine (PEI) to form the desired PEI/PTSAF‐supported CuSO4 NPs catalyst (CuSO4NPs@PEI/PTSAF) have been fabricated. Characterization of the as‐synthesized catalyst by inductively coupled plasma (ICP), Fourier transform infrared (FTIR), X‐Ray diffraction (XRD), scanning electron microscopy (SEM), energy‐dispersive spectroscopy (EDX) and elemental mapping analysis, transmission electron microscopy (TEM), and thermogravity analysis (TGA) demonstrated successful immobilization of the CuSO4 NPs on the PEI/PTSAF composite. This novel catalyst was highly active in the one‐pot A3 and decarboxylative A3 coupling reactions toward generating corresponding propargylamines in good to excellent yields under solvent‐free reaction. The nature of the well distribution of CuSO4 NPs coordinated with PEI ligand in the CuSO4NPs@PEI/PTSAF composite leads to superior catalytic activity. The present methodology offers several advantages such as high catalytic activity, good to excellent yields, short reaction times, simple operations, compatibility of broad scope of substrates, and environmental friendliness. More importantly, the catalyst can be easily recovered from the reaction mixture by a simple filtration and still exhibits remarkable reusability with only marginal loss of its performance after five consecutive runs.

Solvent-free synthesis of propargylamines: an overview

“…Recently, Li et al achieved the synthesis of propargylamines through A 3 coupling catalyzed by CuSO 4 nanoparticles anchored on the surface of polymeric composites. 66 This novel catalyst produced the desired propargylamines in good to excellent yields under solvent-free conditions. The catalyst was recovered and reused upto five times without considerable loss in catalytic efficiency.…”

CuSO4 nanoparticles loaded on carboxymethylcellulose/polyaniline composites: A highly efficient catalyst with enhanced catalytic activity in the synthesis of propargylamines, benzofurans, and 1,2,3‐triazoles

“…[30] In Figure 1c, the S 2p peak at 168.5 eV matched the reported values of the binding energy of S from CuSO 4 . [32,33] The C 1s XPS spectra in Figure 1d exhibited the peak with binding energies of 284.7 eV, which were attributed to the presence of carbon-containing groups. Figure 1e depicted two distinct peaks centered at 401.3 and 399.2 eV corresponding N 1s , which can be ascribed to benzenoid amine and protonated amine in the PANI components, [34] respectively.…”

Ionic liquid containing high-density polyethylene supported tungstate: a novel, efficient, and highly recoverable catalyst

“…Some attractive supports that have been used for the heterogenization of the catalysts are molecular sieves ( Rimaz et al, 2022 ; Gao et al, 2023 ), magnetic nanoparticles ( Xie and Wang, 2021 ; Xie and Li, 2023 ), montmorillonite ( Chellapandi and Madhumitha, 2022 ; Liu et al, 2023 ), commercial silica ( Peron et al, 2021 ; Chandrashekhar et al, 2022 ), two-dimensional manganese dioxide (MnO 2 ) ( Das et al, 2020 ), and metal-organic frameworks (MOFs) ( Goetjen et al, 2020 ; Lin et al, 2022 ). In particular, polymeric materials have drawn a lot of interest as potential catalytic support due to their high stability, easy synthesis and functionalization, and strong corrosion resistance ( Gokmen and Du Prez, 2012 ; Shi et al, 2013 ; Aziz and Islam, 2018 ; Jiang et al, 2021 ; Jiang et al, 2022 ). Moreover, functionalized polymers are extensively employed in various industries such as packaging ( Wan et al, 2020 ), transportation ( Sarkar et al, 2019 ), biomedical engineering ( Szymczyk-Ziółkowska et al, 2020 ), sporting goods ( Sharma et al, 2020 ), electronics ( Zhang et al, 2020 ), energy storage ( Zhang et al, 2021 ), and water treatment ( Khodakarami and Bagheri, 2021 ; Das et al, 2023 ).…”