A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

Abstract

In recent years, many inorganic silica/carbon-based and magnetic materials have been selected to arrest copper ions through a widespread range of anchoring and embedding methodologies. These inorganic supported nanocatalysts have been found to be efficient, environmentally friendly, recyclable, and durable. In addition, one of the vital issues for expanding new, stable, and reusable catalysts is the discovery of unique catalysts. The basis and foundation of this review article is to consider the recently published developments (2014–2019) in the synthesis and catalytic applications of copper supported by silica nanocomposites, carbon nanocomposites, and magnetic nanocomposites for expanding the “click” chemistry.

Copper(I) Complex of Dihydro Bis(2‐Mercapto Benzimidazolyl) Borate as an Efficient Homogeneous Catalyst for the Synthesis of 2H‐Indazoles and 5‐Substituted 1H‐Tetrazoles

“…[3][4][5][6][7][8][9][10][11] Therefore, it is safe to assume that N-Heterocycle compounds play a major role in the biological aspects living organisms. [12][13][14][15][16][17][18][19][20] In addition, some drug molecules bear indazole and tetrazole moieties, examples of which include axitinib (anticancer), [21] pazopanib, bendazac (votrient, tyrosine kinase inhibitor), [22,23] valsartan (antihypertensive agent, angiotensin II receptor), [24,25] cefotiam (a wide spectrum antibiotic against both gram-positive and gram-negative microorganisms), [26] and pemirolast (a mast cell stabilizer that acts as antiallergic agent), [27] as shown in Figure 1.…”

“…Among various types of N ‐heterocyclic compounds, indazoles and tetrazoles as key intermediates in many therapeutically active molecules and natural products, [1,2] exhibit diverse biological activities including antimicrobial, antitumor, HIV‐protease inhibition, antiinflammatory, and antibiotics [3–11] . Therefore, it is safe to assume that N ‐Heterocycle compounds play a major role in the biological aspects living organisms [12–20] …”

Cu2+ ion crosslinked carboxymethylcellulose/diatomite composite beads as an efficient catalyst for CuAAC reactions

“…Since then, CuAAC reaction has become one of the most powerful tools in diverse fields such as drug discovery, 4 polymer chemistry, 5 and material science 6 . Recently, some reviews have outlined the latest progress of CuAAC reactions, and a large variety of copper catalysts have been criticized in these surveys 7‐12 . Based on the Schwartz's modern definitions for homogeneous and heterogeneous catalysis, 13 heterogeneous catalysts have multiple types of active sites and homogeneous catalysts have a single type of active site.…”

“…Based on the Schwartz's modern definitions for homogeneous and heterogeneous catalysis, 13 heterogeneous catalysts have multiple types of active sites and homogeneous catalysts have a single type of active site. In these reviews, both homogeneous and heterogeneous copper catalysts have been discussed 8‐11 . According to the nature of the catalyst precursor, these reported copper catalysts can be categorized into copper(I) or copper(II) salts or complexes, metallic or nanoparticulated copper, and several solid‐supported copper systems 11 .…”

Synthesis of 6,7-Dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by Azomethine Imine-Alkyne Cycloadditions Using Immobilized Cu(II)-Catalysts

“…In extension, we were interested in the use of immobilized Cu(II) complexes with enaminone-type ligands attached to the solid support in CuAIAC reactions. In contrast to the rather extensive use of immobilized copper complexes in azide-alkyne cycloadditions (CuAAC) [ 62 ], their applications in CuAIAC reactions are almost unknown [ 26 ]. 3-Aminopropyl silica gel-immobilized Cu(II)-enaminone complexes would be easy to prepare via a transamination reaction [ 28 , 29 , 30 , 31 , 32 , 33 , 63 , 64 ], could serve as heterogeneous Cu(II) catalysts for the synthesis of pyrazolo[1,2- a ]pyrazoles, and would complement well the known examples of heterogeneous Cu(0)- [ 41 ], Cu(I)- [ 65 , 66 , 67 , 68 , 69 ], and Cu(II)-catalysts [ 26 ] in the CuAIAC reaction.…”