Copper Nanoparticles Supported on Agarose as a Bioorganic and Degradable Polymer for Multicomponent Click Synthesis of 1,2,3-Triazoles under Low Copper Loading in Water

Jeddi, Neda

doi:10.1021/sc500395b

Cited by 79 publications

(64 citation statements)

References 60 publications

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“…However, in most cases, strategies had to be developed in order to prevent CuNPs agglomeration [147], enabling the stability of small CuNPs and high activity toward CuAAC. For example, agarose was a cheap and degradable polysaccharide for the stabilization of active CuNP (CuNPs@agarose) in the size range of 4-8 nm in water under low catalyst loading and mild reaction conditions [148]. The 3-aminopropylsilica support was able to stabilize smaller CuNPs with the size in the range of 1-4.5 nm, leading to very high catalytic activity (productivity up to 1689 mol/mol) in continuous-flow click reaction between phenyl acetylene and benzyl azide [149].…”

Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

View full text Add to dashboard Cite

show abstract

“…75 The catalyst was used in the click synthesis of 1,4-disubstituted 1,2,3-triazoles (16) in green solvent water. The catalyst was described by EDX, SEM, TGA, TEM and XRD.…”

Section: Scheme 15mentioning

confidence: 99%

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

Lal¹,

Rani²

2016

Arkivoc

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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.

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“…Over the years, C−C bond formation reactions like Heck, Suzuki,–, several other coupling reactions– and click reaction mainly triazole and tetrazole formation,− occupied supreme position in organic synthesis. Suzuki reaction mainly utilized for aryl‐aryl bond formation but Heck reaction used for aryl‐vinyl bond formation.…”

Section: Introductionmentioning

confidence: 99%

Development of Synergistic, Dual Pd‐Cu@rGO Catalyst for Suzuki, Heck and Click Reactions: Facile Synthesis of Triazole or Tetrazole Containing Biaryls and Stilbenes

et al. 2018

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A dual synergistic Pd−Cu@rGO catalyst was synthesized and characterized by various analytical techniques. From powder X‐ray diffraction, Raman, FT‐IR and X‐ray photoelectron spectroscopy analysis it was evident that graphite oxide was reduced during decoration with metal nanoparticles on its surface. The percentages of Cu and Pd in the catalyst was also evident from inductive coupled plasma‐atomic emission spectroscopy analysis. After the preparation and characterization of the catalyst, it was employed in Suzuki and Heck reactions. It was also established that the catalyst was efficient in tetrazole and triazoles synthesis (Click reaction). Further, the present catalyst was effective in furnishing the biaryls/stilbenes and tetrazoles/triazoles skeletons in the same organic compound via step wise reactions. The catalyst also showed good catalytic activity in gram scale reaction. The catalyst could be recycled and reused up to seven consecutive runs without not much loss in its catalytic activity. It was evident from TEM, SEM, EDX and FT‐IR analysis that the general morphology and characteristic of reused Pd−Cu@rGO remained almost unchanged.

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Copper Nanoparticles Supported on Agarose as a Bioorganic and Degradable Polymer for Multicomponent Click Synthesis of 1,2,3-Triazoles under Low Copper Loading in Water

Cited by 79 publications

References 60 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

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

Development of Synergistic, Dual Pd‐Cu@rGO Catalyst for Suzuki, Heck and Click Reactions: Facile Synthesis of Triazole or Tetrazole Containing Biaryls and Stilbenes

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