Solvent-free synthesis of 1,4-disubstituted 1,2,3-triazoles using a low amount of Cu(PPh3)2NO3 complex

Wang, Dong; Li, Na; Zhao, Mingming; Shi, Weilin; Ma, Chaowei; Chen, Baohua

doi:10.1039/c0gc00381f

Cited by 139 publications

(50 citation statements)

References 37 publications

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“…1,3‐Cycloaddition reactions of azides with olefins provide direct access to a wide range of 1,2,3‐triazoles as useful heterocyclic systems with remarkably stable aromatic structures, which can serve, among other roles, as structural analogues of a peptide linkage . Copper catalysts accelerate the cycloaddition reactions of azides with such terminal alkynes by a factor of at least 106 relative to the uncatalysed case and copper‐catalysed azide–alkyne cycloaddition (CuAAC) is a well‐established methodology in modern organic synthesis …”

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confidence: 99%

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Amini

Nikkhoo

Farnia

2017

Applied Organom Chemis

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Readily prepared copper(II) immobilized on layered double hydroxide has been found to effectively catalyse the 1,3‐dipolar cycloaddition (CuAAC) of a variety terminal alkynes and benzyl azides generated in situ from sodium azide and benzyl halides furnishing the corresponding 1,2,3‐triazoles in excellent yields. The advantages of the protocol are short reaction time, mild reaction conditions, reusability of the catalyst and applicability to a wide range of substrates.

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confidence: 99%

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Amini

Nikkhoo

Farnia

2017

Applied Organom Chemis

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“…Similarly the reaction between allyl bromide, propargyl dimethyl malonate and sodium azide was more efficient with SLS and TPGS-750-M with respect to the use of pure water (Table 4, entry 16). The reaction of allyl bromide with several aromatic alkynes in SLS as well as in TPGS-750-M yielded quantitative formation of the corresponding triazoles in 30 min, while in pure water the reactivity was much lower especially with less substituted aromatic alkynes (Table 4, entries [17][18][19]. For the highly reactive alkynes reported in Table 4, entries 20 and 21, the reaction was carried out with only 0.5 mol% 1 for 15 minutes at rt observing good to excellent triazole formation in the presence of the selected surfactants while the reaction did not occur in pure water.…”

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Micellar promoted multi-component synthesis of 1,2,3-triazoles in water at room temperature

et al. 2015

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“…Click reaction was carried out by several homogeneous catalysts such as, CuSO 4 /sodium ascorbate/H 2 O, CuI/PEG‐400, and Cu(OAc) 2 /H 2 O, Cu(PPh 3 )NO 3 , PTA‐iminophosphorane, nitrogen containing ligands [(NHC)CuX] exhibiting higher selectivity and activity. However, some of these catalysts suffer high metal loading, difficult to recover along with some metal contaminates in the end product.…”

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confidence: 99%

SO₃Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction

2019

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A novel heterogeneous carbon-based sulfonated copper (SO 3 Cu-carbon) catalyst was developed for the first time and investigated its catalytic activity for the regioselective synthesis of β-hydroxy 1,2,3-triazoles by azide-alkyne cycloaddition in aqueous medium. The SO 3 Cu-carbon catalyst was prepared by the modification of the glycerol-based SO 3 H-carbon catalyst on treatment with 10% aqueous CuCl 2 solution under controlled conditions. Based on its physico-chemical characteristics the structure of the catalyst is proposed as a polycyclic aromatic carbon attached with -SO 3 Cu, -COOCu and -OCu functionalities. The catalytic activity of the SO 3 Cu-carbon catalyst was demon-strated for the one pot 'click' reaction of epoxide, sodium azide and terminal alkyne in water at 60°C for the synthesis of βhydroxy 1,2,3-triazoles in excellent yields (89-94%) without any additives. The formation of the product proceeds in one pot through a mechanism that involves in situ generation of organic azide intermediate followed by rapid ring closure with alkynes. The catalyst was easily recovered by simple filtration and reused for 5 cycles without any leaching and deactivation thus exhibiting its excellent stability and reusability. Moreover, the cascade reaction was best performed in water at moderate temperature, rendering all the processes truly green.[a] G. recyclability makes this methodology operationally convenient and does not require additives. 2 3 4 5 6 7 8

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Solvent-free synthesis of 1,4-disubstituted 1,2,3-triazoles using a low amount of Cu(PPh3)2NO3 complex

Cited by 139 publications

References 37 publications

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Micellar promoted multi-component synthesis of 1,2,3-triazoles in water at room temperature

SO₃Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction

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Solvent-free synthesis of 1,4-disubstituted 1,2,3-triazoles using a low amount of Cu(PPh3)2NO3 complex

Cited by 139 publications

References 37 publications

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Micellar promoted multi-component synthesis of 1,2,3-triazoles in water at room temperature

SO3Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction

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SO₃Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction