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Upstream product

• 536-74-3 phenylacetylene 
• 159979-96-1 4-fluorobenzyl azide 
• 932-88-7 1-iodo-2-phenylethyne 
• 459-46-1 4-Fluorobenzyl bromide 
• 352-11-4 1-chloromethyl-4-fluorobenzene 

Relevant academic research and scientific papers

Pyrazine Based Type-I Sensitizing Assemblies for Photoreduction of Cu(II) in ‘One-Pot Three-Component’ CuAAC Reaction Under Aerial Conditions

Photosensitizing assemblies of pyrazine derivative PDA have been developed which exhibit a high photostability, ‘lighted’ excited state, balanced redox potential, high transportation potential and activate oxygen via type-I pathway only. These PDA assemblies in combination with Cu(II) ions catalyze the CuAAC reaction via in situ reduction of Cu(II) ions without any reducing or stabilizing agent. The present protocol has wide substrate scope with recyclability of the catalytic system up to six catalytic cycles and is applicable to gram-scale synthesis.

Copper immobilized on biomimetic assembled calcium carbonate/carboxymethylcellulose hybrid: a highly active recoverable catalyst for CuAAC reactions

A novel copper immobilized on biomimetic assembled carboxymethylcellulose/calcium carbonate hybrid (CuII@CMC/CaCO3) as an efficient heterogeneous catalyst for the synthesis of 1,2,3-triazoles has been described herein. The fabrication of CuII@CMC/CaCO3 is accomplished through a bioinspired mineralization process using sodium carboxymethylcellulose (CMC-Na) as the template and ion exchange agent, while the metathesis, nucleation, assemble, hybridization, and immobilization of Cu(II) occurred by successful treatment with CaCl2, Na2CO3, and CuSO4 in water at room temperature. The resultant CuII@CMC/CaCO3 hybrid was well characterized by various analyses such as FT-IR, XRD, SEM, EDX, EDX-mapping, TEM, and TGA techniques. In the presence of low copper loading of CuII@CMC/CaCO3 hybrid, benzylic halides, azide, and alkynes proceeded smoothly to afford 1,4-disubstituted 1,2,3-triazoles in high yields. The catalyst can be conveniently recovered from the reaction mixture by filter and reused for at least 5 consecutive runs with a slight drop in its catalytic activity. The remarkable activity and stability of the catalyst may be attributed to the coordination of both carboxyl and hydroxyl groups of the hybrid of CMC/CaCO3.

Highly Efficient and Stable Atomically Dispersed Cu Catalyst for Azide-Alkyne Cycloaddition Reaction

In this study, we report a highly stable and efficient single-atom Cu dispersed on N-doped porous carbon as a superior catalyst for azide-alkyne cycloaddition reaction. A broad set of 1,4-disubstituted 1,2,3-triazoles was synthesized in high to excellent

Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy

Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.

Click reactions catalyzed by Cu(I) complexes supported with dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine ligands

Four Cu(I) complexes bearing dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine co-ligands were synthesized and their catalytic activity was investigated in azide-alkyne reactions. These complexes were tested as catalyst system and among them a Cu(

Harnessing the Untapped Catalytic Potential of a CoFe2O4/Mn-BDC Hybrid MOF Composite for Obtaining a Multitude of 1,4-Disubstituted 1,2,3-Triazole Scaffolds

Metal-organic frameworks derived nanostructures with extraordinary variability, and many unprecedented properties have recently emerged as promising catalytic materials to address the challenges in the field of modern organic synthesis. In this contribution, the present work reports the fabrication of an intricately designed magnetic MOF composite based on Mn-BDC (manganese benzene-1,4-dicarboxylate/manganese terephthalate) microflakes via a facile and benign in situ solvothermal approach. Structural information about the as-synthesized hybrid composite has been obtained with characterization techniques such as TEM, SEM, XRD, FT-IR, AAS, EDX, ED-XRF, and VSM analysis. Upon investigation of catalytic performance, the resulting material unveils remarkable efficacy toward facile access of a diverse array of pharmaceutically active 1,2,3-triazoles from a multicomponent coupling reaction of terminal alkynes, sodium azide, and alkyl or aryl halides as coupling partners. In addition to a wide substrate scope, the catalyst with highly accessible active sites also possesses a stable catalytic metal center along with superb magnetic properties that facilitate rapid and efficient separation. The prominent feature that makes this protocol highly desirable is the ambient and greener reaction conditions in comparison to literature precedents reported to date. Further, a plausible mechanistic pathway is also proposed to rationalize the impressive potential of the developed catalytic system in the concerned reaction. We envision that findings from our study would not only provide new insights into the judicious design of advanced MOF based architectures but also pave the way toward greening of industrial manufacturing processes to tackle critical environmental and economic issues.

Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide-alkyne cycloaddition type reactions in water

A novel sustainable hydrogel catalyst based on the reaction of sodium alginate naturally extracted from brown algaeLaminaria digitataresidue with copper(ii) was prepared as spherical beads, namely Cu(ii)-alginate hydrogel (Cu(ii)-AHG). The morphology and

A comparison of the catalytic efficiency of copper-based bimetallic nanoparticles in the click reactions

Compared to monometallic nanoparticles, bimetallic nanoparticles have attracted wide attention due to their physical properties, excellent catalytic activity, high regioselectivity, selectivity, and stability. Here, we have first synthesized 10 different kinds of graphene quantum dot–stabilized Cu-based bimetallic nanoparticles (including CoCu, NiCu, RuCu, RhCu, PdCu, AgCu, IrCu, AuCu, FeCu, and PtCu) and compared their catalytic activities in a CuAAC click reaction. Among them, RhCu provides the highest yield of the desired product in the click reaction (77%). The catalytic activity of these MCu in the click reaction is in the order: RhCu > PdCu > AuCu > CoCu > PtCu > AgCu > NiCu > CuNP > RuCu > FeCu > IrCu.

An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions

Within the green chemistry context, heterogeneous catalysis for the synthesis of N-heterocycles from renewable resources using non-precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ～1218 m2 g?1, huge pore volumeγτ“;6 mL g?1 and dual micro/mesopore architectures. Subsequent Cu-coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu-HMOP) to accomplish multi-step cascade reactions for preparation of N-heterocycles by different routes. For instance, the Cu-HMOP efficiently catalyzes one-pot sequential multi-step oxidative dehydrogenative coupling of 2-aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides-alkynes, the Cu-HMOP produced quantitative yield for 1,4-disubstituted 1,2,3-triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu-HMOP catalysts shows a consistent activity in the multi-component quinoline synthesis as model reaction.

Hyperbranched polyethylenimine-supported copper(II) ions as a macroliganted homogenous catalyst for strict click reactions of azides and alkynes in water

Loading hyperbranched polyethylenimine (PEI) with copper(II) ions leads to the formation of a new water-soluble metallodendritic polymer Cu(II)-PEI that has been found to effectively catalyze the clickable azide-alkyne [3 + 2] cycloaddition reactions in w