Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction

Tavassoli, Mahnaz; Landarani‐Isfahani, Amir; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor‐Baltork, Iraj

doi:10.1016/j.apcata.2015.07.015

Cited by 33 publications

(16 citation statements)

References 53 publications

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“…The catalyst 18 was also successfully used for the formation of aryl–sulphur bonds in aqueous media [ 50 ]. In the next work [ 51 ], the heterogeneous catalyst 19 based on a copper(II) complex of 1,2-bis(4-pyridylthio)ethane anchored on chloromethylated polystyrene was prepared ( Scheme 12 ). Catalyst 19 was tested for three-component reaction of organic halides, sodium azide and alkynes, which was performed in the presence of sodium ascorbate as a reduction agent in poly(ethylene glycol) (PEG-400), (0.2 mol % Cu), at 65 °C, 10–25 min.…”

Section: Carbon–nitrogen Forming Reactionsmentioning

confidence: 99%

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Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Drabina¹,

Svoboda²,

Sedlák³

2017

Molecules

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This present mini-review covers recently published results on Cu(I) and Cu(II) complexes immobilized on polystyrene carriers, which are used as heterogeneous, eco-friendly reusable catalysts applied for carbon–carbon and carbon–nitrogen forming reactions. Recent advances and trends in this area are demonstrated in the examples of oxidative homocoupling of terminal alkynes, the synthesis of propargylamines, nitroaldolization reactions, azide alkyne cycloaddition, N-arylation of nitrogen containing compounds, aza-Michael additions, asymmetric Friedel–Crafts reactions, asymmetric Mukaiyama aldol reactions, and asymmetric 1,3-dipolar cycloaddition of azomethine ylides. The type of polystyrene matrix used for the immobilization of complexes is discussed in this paper, and particularly, the efficiency of the catalysts from the point of view of the overall reaction yield, and possible enantioselectivity and potential reusing, is reviewed.

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Section: Carbon–nitrogen Forming Reactionsmentioning

confidence: 99%

“…The recovery and reuse of catalyst 19 was successfully confirmed with the same three-component reaction (Cycle 1: 99%; Cycle 4: 95%; Cycle 7: 93%) ( Scheme 12 ). This catalytic system also showed excellent activity for the synthesis of bis -1,4-disubstituted 1,2,3-triazoles (66–88%) [ 51 ].…”

Section: Carbon–nitrogen Forming Reactionsmentioning

confidence: 99%

Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Drabina¹,

Svoboda²,

Sedlák³

2017

Molecules

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“…The copper is stabilized with different ligands which are finally supported on solid supports. Many types of ligands (including dithioethane, L‐proline, 1,10‐phenanthroline, tris (triazolyl)methanol, and 1 H ‐pyrrole‐2‐carbohydrazide) have been attached on solid materials and applied in laboratory or industrial processes. On the other hand, one of the most important factors must be considered in developing new catalysts is to enhance the capacity of metal absorption of solid supports by using complexation in two or multi‐functionalized ligands as stabilizers .…”

Section: Introductionmentioning

confidence: 99%

Supported benzimidazole‐salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one‐pot synthesis of hybrid molecules

Sharghi

Aberi

Shiri

2018

Applied Organom Chemis

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A novel and efficient nanocatalyst consisting of benzimidazole‐salen Cu(II) complex on surface‐modified silica (BS‐Cu(II)@SiO2) was prepared. The heterogeneous nanocatalyst was characterized by FESEM, TEM, EDX, FT‐IR, XRD, ICP, and TGA. The nanocatalyst was used for the one‐pot synthesis of some target hybrid molecules. An efficient four component C–H bond activation/[3 + 2] cycloaddition and condensation/cyclization/aromatization sequence toward triazole‐benzimidazole derivatives is disclosed. This methodology provides a general and rapid synthetic route to some new triazole‐benzimidazole hybrids under mild reaction conditions. In addition, the heterogeneous nanocatalyst can be easily separated from the reaction mixture and used several times without noticeable leaching or loss of its catalytic activity. We believe this interesting one‐pot reaction as well as benzimidazole‐salen Cu(II) complex pave the way to the design and synthesis of other new hybrid molecules and metal catalysts, respectively.

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“…Although good catalytic activities of these ILs presented, they have some disadvantages such as partially ILs wasted and difficulties in the separation and recycle. A useful method to surmount these shortages is the development of supported ILs catalysts [33][34][35][36][37][38][39], which could transfer the catalytic reactions from homogeneous catalysis to a type of heterogeneous catalysis. In this case, attractive features such as gaining high catalyst efficiency and stability, facilitating the catalyst recovery and excellent reusability have been achieved [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Preparation of Silica Supported Ionic Liquids for Highly Selective Hydroxylation of Aromatics with Hydrogen Peroxide under Solvent-free Conditions

Fang

2017

J. Mex. Chem. Soc.

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A series of silica supported functionalized ionic liquid catalysts have been prepared and tested in the hydroxylation of aromatics to phenols with H2O2 under solvent-free conditions. The properties of the heterogeneous catalytic system were studied by tuning various reaction parameters including selection of catalyst, amount of the catalyst, influences of reaction time and temperature. Among the catalysts, CuCl3-IL-SiO2 exhibited the highest efficiency in the hydroxylation of aromatics to phenols under the optimized condition along with good recycle performance.

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Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction

Cited by 33 publications

References 53 publications

Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Supported benzimidazole‐salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one‐pot synthesis of hybrid molecules

Preparation of Silica Supported Ionic Liquids for Highly Selective Hydroxylation of Aromatics with Hydrogen Peroxide under Solvent-free Conditions

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