Copper iodide nanoparticles on poly(4-vinyl pyridine) as new and green catalyst for multicomponent click synthesis of 1,4-disubstituted-l,2,3-triazoles in water

Poly(4-vinyl pyridine) supported nanoparticle of copper(Ⅰ) iodide is reported as a green and recyclable catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides,sodium azide and terminal alkynes in water. This catalyst can be recovered by simple filtration and recycled up to 8 consecutive runs without any loss of its efficiency.     

Click synthesis of 1,4-disubstituted-1,2,3-triazoles catalyzed by melamine-supported CuO nanoparticles as an efficient recyclable catalyst in water

Melamine-supported CuO nanoparticles (M-CuO nanocatalyst) are prepared as a new and efficient recyclable nanocatalyst for the regioselective synthesis of 1,2,3-triazoles in water. This new nanocatalyst was prepared by co-precipitation method and characterized by FT-IR spectral study, TGA, DSC, XRF, ICP-OES, XRD, SEM, EDS and BET analysis. A wide range of 1,4-disubstituted-1,2,3-triazoles were synthesized from reaction of benzyl halides or alkyl halides with phenyl acetylene and sodium azide in high yields. M-CuO nanocatalyst could be reused more than 6 times without considerable loss of its initial activity.

     

Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles

A three-component coupling was used to prepare a series of 1,4-disubstituted-1,2,3-triazoles from the corresponding acetylated Baylis-Hillman adducts, sodium azide and terminal alkynes. This one-pot reaction further increases the efficacy of ‘Click’ synthesis and diversifies the preparation of multi-functional 1,4-disubstituted-1,2,3-triazoles.     

A recyclable/reusable hydrotalcite supported copper nano catalyst for 1,4-disubstituted-1,2,3-triazole synthesis via click chemistry approach

Using hydrotalcite as solid support, copper nano particles were synthesized and used in azide-alkyne cycloaddition reaction en route to the synthesis of 1,4-disubstituted-1,2,3-triazoles. The catalyst is heterogeneous and can be recycled and reused easily. Room temperature reaction condition and the use of ethylene glycol as solvent make it an environment friendly system.     

Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system

A copper(I) catalyst in a mixture of the ionic liquid [bmim][BF₄] and water, can effect three-component reaction of halides, sodium azide and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to high yields. The method is efficient and environmentally friendly.     

Copper-catalyzed azide-alkyne cycloaddition reaction in water using cyclodextrin as a phase transfer catalyst

1,4-Disubstituted-1,2,3-triazoles were obtained in excellent yields from azides and terminal alkynes in H(2)O in the presence of catalytic amount of β-cyclodextrin as a phase transfer catalyst. Also, a one-pot CuAAC reaction was carried out successfully, affording 1,4-disubstituted-1,2,3-triazoles in good to high yields starting from an alkyl bromide, sodium azide, and terminal alkyne.     

Nano-copper catalyzed three-component reaction to construct 1,4-substituted 1,2,3-triazoles

Three-component reaction of alkyl halides, sodium azide with terminal alkynes can be catalyzed by nano-copper particles under ambient conditions. A series of 1,4-disubstituted-1,2,3-triazoles were obtained regioselectively by this one-pot strategy. Nano copper can be reused at least three times without significant deactivation.     

A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction

A microwave-assisted three-component reaction was used to prepare a series of 1,4-disubstituted-1,2,3-triazoles from corresponding alkyl halides, sodium azide, and alkynes. This procedure eliminates the need to handle organic azides, as they are generated in situ, making this already powerful click process even more user-friendly and safe.     

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by Reusable AlCl3 Immobilized on γ-Al2O3

There is rapidly growing interest in the synthesis and use of substituted 1,2,3-triazoles. We report an easy and interesting procedure that demonstrates the effectiveness of surface-modified γ-Al₂O₃, which is reusable, efficient, catalytic, safe, and environmentally acceptable for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via [3 + 2] cycloaddition of phenyl and benzyl azides with a series of aryl nitroolefins in good yields. No adverse effect on substituents such as nitro, cyano, hydroxy, ether linkage, and halogens was observed. The catalyst could easily be recycled and was reused for nine runs without losing its activity.     

Facile One-Pot Synthesis of 1,2,3-Triazoles Featuring Oxygen,Nitrogen, and Sulfur Functionalized Pendant Arms

A practical and efficient one-pot synthesis of novel 1,2,3-triazoles featuring nitrogen, oxygen, and sulfur functionalized pendant arms has been developed. The click reaction of mono-propargyl derivatives supported by aniline, thiophenol, and benzyl alcohol, with sodium azide and p-substituted benzyl halogenides, renders a series of N-substituted-1,2,3-triazoles in good yields under mild reaction conditions. The catalyst system was based in Cu(OAc)₂ · H₂O, sodium L-ascorbate, and 1,10-phenanthroline monohydrate, and all reactions were performed in a mixture H₂O–ethanol (4:1 v/v). Additionally, the preparation of bis-1,2,3-triazoles supported by di-propargylated aniline was carried out, demonstrating the versatility of the present methodology.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]     

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 (Cu^II@CMC/CaCO₃) as an efficient heterogeneous catalyst for the synthesis of 1,2,3-triazoles has been described herein. The fabrication of Cu^II@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 Cu^II@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 Cu^II@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.

     

Synthesis of novel 1,4-disubstituted 1,2,3-triazoles bearing organosilicon-sulfur groups via the click reaction sonocatalyzed by LaCuxMn1-xO3 nanoparticles

A highly efficient and environmentally friendly one-pot procedure for the synthesis of 1,2,3-triazoles by 1,3-dipolar cycloaddition of benzyl halides, terminal alkynes, and sodium azide over LaCu_xMn_1-xO₃ perovskite oxides was developed. LaCu_0.7Mn_0.3O₃ was found to be active with low catalyst loading under ultrasonic irradiation in aqueous media. The reaction was performed efficiently in the presence of the nanocatalyst in the absence of any additive or base with a noticeable reduction in the reaction time. The catalyst could be recycled and reused at least five times without any significant effect on the results of the reaction. Moreover, a series of novel organosilicon-sulfur substituted 1,2,3-triazole derivatives was synthesized using carbon disulfide and tris(trimethylsilyl)methylithium.     

Synthesis of 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones via copper-(I)-catalyzed alkyne-azide 'click chemistry' and their reactivity

In this paper we present the room temperature synthesis of a novel serie of 1,4-disubstituted-1,2,3-triazoles 4a-l by employing the (3+2) cycloaddition reaction of pyrimidinones containing alkyne functions with different model azides in the presence of copper sulphate and sodium ascorbate. To obtain the final triazoles, we also synthesized the major precursors 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones 3a-r from ethyl 2,2-dicyanovinylcarbamate derivatives 2a-c and various primary aromatic amines containing an alkyne group. The triazoles were prepared in good to very good yields.     

Polymer-Supported Azide and Copper(I): Green Reusable Reagent and Catalyst for Click Cyclization

In this work, polymer-supported copper(I) iodide catalyst and macroporous polymer-supported azide reagent were used to simplify the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-bromo ketones/amides/esters following green chemistry principles. This new one-pot protocol facilitates the workup of the reaction and provides the products in short times and excellent yields. Heterogeneous catalyst and reagent can be reused at least for five runs without significant yield decreases.     

[bmim]BF4/[Cu(Im12)2]CuCl2 as a novel catalytic reaction medium for click cyclization

Herein, a new application of an ionic liquid containing copper (I), ([Cu(Im¹²)₂]CuCl₂), is introduced. This ionic liquid was used as an efficient catalyst for the click cyclization between organic azides and terminal alkynes in various solvents. Then, the mixture of [bmim]BF₄/[Cu(Im¹²)₂]CuCl₂ was used as a green catalytic medium for the multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-halo ketones. The reactions were performed efficiently in this mixture and excellent yields were obtained in all cases. This catalytic reaction medium was recycled five times without significant loss of activity.     

Reusable polymer-supported copper catalyst for one-pot synthesis of 1-alkyl- and 1-aryl-1,2,3-triazoles: green,simple, and effective

Abstract

Polymer-supported copper-catalyzed one-pot synthesis of 1,4-disubstituted 1-alkyl- and 1-aryl-1,2,3-triazoles via 1,3-dipolar cycloaddition of alkyl halides or arylboronic acids, sodium azide, and phenylacetylene has been developed. Reactions went smoothly at room temperature using PEG/H₂O or methanol as solvent to afford the corresponding triazoles in good to excellent yields. The catalyst could be recovered by simple filtration and reused several times with slightly decrease in its activity.     

Ionic Liquid Containing Copper(I): A New,Green, Homogeneous,and Reusable Catalyst for Click Cyclization

An ionic liquid containing copper(I) is introduced as a new, green, homogeneous, and reusable catalyst for click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-azido ketones and terminal alkynes in various solvents, especially in [bmim]BF₄. These cyclization reactions were efficiently performed in the presence of introduced ionic liquid catalyst with short reaction times and good yields. This catalytic ionic liquid exhibits excellent activity and can be simply recovered and reused for at least five runs without any loss in its activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

Preparation of Cu(OAc)2/MCM‐41 catalyst and its application in the one‐pot synthesis of 1,2,3‐triazoles in water

An efficient one‐pot synthesis of 1,2,3‐triazoles via the three‐component coupling reaction between benzyl or alkyl bromides, terminal alkynes, and sodium azide in the presence of catalytic amounts of Cu(OAc)₂/MCM‐41 catalyst has been described. This catalyst showed high catalytic activity and 1,4‐regioselectivity for the [3 + 2]Huisgen cycloaddition. This method avoids isolation and handling of organic azides, using water as a solvent, and catalyst recycling makes this synthesis a truly green procedure. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:415–421, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21031     

The one-pot synthesis of 4-aryl-1H-1,2,3-triazoles without azides and metal catalization

In this study, a new methodology for the one-pot synthesis of 4-aryl-1H-1,2,3-triazoles from arylglyoxaldoxime semicarbazone is presented. 4-Aryl-1,2,3-triazoles were obtained in moderate to good yields via sodium dithionite and O₂, which are all efficient, safe and inexpensive reagents. This reaction is more suitable for large-scale syntheses than those using hydrazoic acid, sodium azide, or organic azides.