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

Abstract

Abstract:The explosively-growing applications of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between organic azides and alkynes (CuAAC) have stimulated an impressive number of reports, in the last years, focusing on recoverable variants of the homogeneous or quasi-homogeneous catalysts. Recent advances in the field are reviewed, with particular emphasis on systems immobilized onto polymeric organic or inorganic supports.

XAFS structural characterization of Cu vapour derived catalysts supported on poly‐4‐vinylpyridine and carbon

“…In any case, this contribution, which requires further investigations, does not affect the main findings related to the presence of Cu(I) oxidized phase NPs in the Cu/PVPy sample that is quite important because able to explain the high catalytic performances observed in the CuAAC catalytic reactions usually catalyzed by Cu(I) species. [9,[14][15][16][17] Moving to the Cu/C sample, in Fig. 2 (right panel), its XANES spectrum is compared to the one of bulk CuO because in both spectra, we find the presence of a weak peak, A.…”

“…[14][15][16][17] Various heterogeneous systems based on Cu NPs immobilized on organic and inorganic supports such as carbon, organic polymers and inorganic oxides were developed because of their advantages in terms of easy recovery and reutilization potential. [14,18] Among them, metal vapour synthesis (MVS) derived Cu NPs, immobilized on 3-aminopropyl functionalized silica, showed high catalytic efficiency both in batch and in packed-bed reactors for continuous-flow CuAAC reactions. [19] The MVS synthetic approach allows to obtain very small Cu NPs (<5 nm) directly usable, without calcination and activation steps that could modify the structure of the organic supports.…”

Photolysis of 5-Azido-3-Phenylisoxazole at Cryogenic Temperature: Formation and Direct Detection of a Nitrosoalkene

“…Additionally, their dipolar character makes them useful for forming new C-N bonds through cycloaddition. For example, the Huisgen 1,3-dipolar cycloaddition of organic azides to alkynes is commonly used to form triazole compounds, which have utility in medicinal and pharmaceutical chemistry [2][3][4]. The pursuit of sustainable chemistry has redirected efforts toward the use of photochemistry for synthetic applications because sunlight, photocatalysts, or eco-friendly light-emitting diodes (LEDs) can be used to drive photoreactions [5].…”

Development of a Turn-On Fluorescent Traceable Linker Employing <i>N</i>-Sulfanylethylcoumarinyl Amide for the Enrichment and Visualization of Target Proteins

“…An alkyne-containing ligand derivative is first covalently connected to the target protein by photo-affinity labeling 1) or an activity-based probe approach. [2][3][4][5] To the resulting target with an alkyne moiety is then attached a linker possessing a biotin moiety and an azide via Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC). [6][7][8][9] Next, the target cross-linked with the biotinylated linker is selectively adsorbed on streptavidin (SAv) beads.…”