Alkyne-Azide Cycloaddition Catalyzed by Fe-Cu Nanoparticles

Garcia-Munoz, Angel; González, Jaime; Trujillo-Reyes, Jessica; Morales‐Luckie, Raúl A.; Sánchez‐Mendieta, Víctor; González, Carlos; Fuentes, A.; Cuevas-Yáñez, Erick

doi:10.2174/157017812800167457

Cited by 5 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction was highly efficient even when performed in vivo; the relief of the ring strain is a powerful driving force that links cyclooctyne to azide. This strategy has also been successfully employed in several other fields. − Another approach that avoids the use of Cu(I) is copper nanoparticles, − which are often used in combination with a ligand, a base, and/or ultrasound , to enhance the rate of the reaction. For example, Yus and co-workers reported that, when 10 mol % copper nanoparticles with sizes of 1–5 nm were used in the presence of triethylamine (TEA), nearly quantitative yields were obtained within 30 min .…”

Section: Introductionmentioning

confidence: 99%

Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers

et al. 2013

View full text Add to dashboard Cite

Syringaldehyde and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cycloaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. In order to produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (< 5% yield). However, it was an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 µM in the DPPH assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed Click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.

show abstract