Copper(I) iodide supported on modified cellulose‐based nano‐magnetite composite as a biodegradable catalyst for the synthesis of 1,2,3‐triazoles

Abstract

Nano‐Fe3O4@Cellulose‐NH2‐CuI as a novel magnetically separable composite was prepared and fully characterized using various techniques including Fourier transform infrared, X‐ray photoelectron and energy‐dispersive X‐ray spectroscopies, X‐ray diffraction, field‐emission scanning and transmission electron microscopies, thermogravimetric analysis and vibrating sample magnetometry. To obtain an appropriate structure and also to describe to some extent the different kinds of metal–ligand interactions present in the nano‐Fe3O4@Cellulose‐NH2‐CuI composite, covalent and electrostatic interactions, density functional theory model chemistry and quantum theory of atoms in molecules method were employed, respectively. This cellulose‐based heterogeneous catalyst can effectively promote the one‐pot three‐component reaction of a variety of terminal alkynes bearing substituted phenyls or propargylic alcohol together with substituted benzyl halides and sodium azide, so‐called click reaction, in water to afford the corresponding 1,4‐disubstituted 1,2,3‐triazoles with improved yields and regioselectivity. The magnetic catalyst was conventionally recovered using an external magnet and reused in at least four successive runs under the optimal reaction conditions, without appreciable loss of its activity.

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

“…It is worth mentioning that the results showed alkyl and aryl halides react better than haloketones in terms of yields and reaction times. The efficiency of CuI@[PMMA‐co‐MI] in click reaction was also compared with that of previously reported catalysts under various reaction conditions (Table ) . By comparison, it can be concluded that CuI@[PMMA‐co‐MI] as a novel nanocatalyst has several merits such as higher or comparable yield of the desired product in shorter reaction time.…”

“…The efficiency of CuI@[PMMA-co-MI] in click reaction was also compared with that of previously reported catalysts under various reaction conditions (Table 7). [11,28,[61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76] By comparison, it can be concluded that CuI@[PMMA-co-MI] as a novel nanocatalyst has several merits such as higher or comparable yield of the desired product in shorter reaction time. It should be mentioned that there are some reports in which higher yields of products were achieved using a low amount of catalyst loading.…”

CuI‐functionalized halloysite nanoclay as an efficient heterogeneous catalyst for promoting click reactions: Combination of experimental and computational chemistry

“…Finally, the efficiency of CuI@HNTs‐2 N‐Sal for the above‐mentioned click reaction was compared with that of some previously reported catalysts under various reaction conditions (Table ) . Comparing the protocols, it can be concluded that use of CuI@HNTs‐2 N‐Sal led to higher or comparable yield of the desired product in shorter short reaction time.…”

Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles

“…Nevertheless, these systems are usually homogeneous and suffer from inherent drawbacks: difficulty in separating the catalyst and product, environmental concern, and recyclability. Recent research in this area has focused on beneficial heterogeneous catalysis which can address these problems and has several advantages such as easier separation of catalyst and product(s), better recovery, allowing for reuse of the catalyst systems, and reduced metal contamination in the final products . In this context, magnetic nanoparticles (MNPs) are considered promising catalysts because of their response to an external magnetic field and are thus extensively used in a variety of important organic reactions .…”