Recent developments in copper nanoparticle-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Abstract

The Cu(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and organic azides generating 1,4-disubstituted 1,2,3-triazoles has attracted considerable attention owing to its consistency, specificity, and biocompatibility. Copper nanoparticles supported on various supports such as agarose, cellulose, chitosan, charcoal, activated carbon, silica gel, aminoclay, polymer support like poly(styrene-co-maleimide) (SMI) and polyvinylpyrrolidone (PVP) have been utilized as heterogeneous catalyst for the synthesis of 1,2,3-triazoles. This review summarizes various straightforward and efficient methods for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles utilizing supported copper nanoparticles as a source of the heterogeneous catalytic species and water as solvent.

Synthesis of fish scale derived hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for highly efficient synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as antifungal agents

“…Additionally, the covalent grafting of active organic molecules like trimethoxysilane derivatives to inorganic networks such as HAP, silica and other mesoporous materials can provide the proper sites for chelation with metal species [13]. In this regard, Cu (I) salts are widely used in OIHCs structure due to the excellent performance of Cu(I) catalyst in 'Click' Huisgen azide-alkyne cycloaddition [14]. Active Cu (I) as a catalyst has an undeniable role in the regioselectivity of the Huisgen cycloaddition reaction and merely acquires 1,4-disubstituted 1,2,3-triazoles isomers.…”

Copper(II)-catalyzed aerobic oxidation of hydrazides to azo intermediates and their Diels–Alder versus ene trapping

“…An initial demonstration of this was exemplified by generating an azo compound that was directly trapped intramolecularly by a diene in situ in excellent yield. 12,13 Although it has been recently shown that certain copper complexes can be used as mild oxidation systems for a number of related reactions, [14][15][16][17][18][19][20] the copper-catalyzed aerobic oxidation of hydrazines and hydrazides to the corresponding azo compounds remains largely unexplored, with one example back in 1948 21 using catalytic CuBr and di-tert butyldiaziridinone as oxidant was reported, however, the resulting azobenzene did not undergo HDA trapping. 22 It has also been recently reported that a CuI-DMAP system oxidizes di-tert-butylhydrazodicarboxylate to the corresponding azodicarboxylate which was used in situ to dehydrogenate 1,2,3,4-tetrahydroquinolines.…”

Nanoparticle‐Catalysed 1,3‐Dipolar Cycloadditions

“…This latter topic appears to be strongly related to the field of “click” chemistry. In fact, several recent authoritative reviews were focused to the following aspects of nanoscale copper‐containing catalysts: ( i ) the multicomponent synthesis of 1,2,3‐triazoles, ( ii ) the “click” chemistry with copper nanoparticles, in water as the solvent, ( iii ) the role of “click” dendrimers in triazole synthesis and ( iv ) the use of CuO nanoparticles in the azide–alkyne cycloaddition …”