PdEDTA Held in an Ionic Liquid Brush as a Highly Efficient and Reusable Catalyst for Suzuki Reactions in Water

Wei, Junfa; Jiao, Jiao; Feng, Jin‐Juan; Lv, Jing; Zhang, Xiru; Shi, Xiao‐Xin; Chen, Zhanguo

doi:10.1021/jo900481y

Cited by 71 publications

(47 citation statements)

References 11 publications

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“…27 The exchange between Cl − and PF General procedure for the selective oxidation of sulfides to sulfoxides…”

Section: Synthesis Of Catalystmentioning

confidence: 99%

“…Recently, it was synthesized a set of silica-supported multilayer ionic liquids (ILs) bearing two or more imidazolium ions on each of the side chains. 27,28 They were called "ionic liquid brushes" because of their brush-like feature. In comparison with the monolayer ILs previously reported, it was expected that our immobilized multiple layer ILs should act as highly active catalysts on the basis of the following characteristics: (i) the brush extends the immobilized ILs to the upper spaces outside the surface of the supports, offering a deeper 3D environment that closely resembles the liquid-phase character of ionic liquids for both hydrophilic and hydrophobic reactants, (ii) more flexibility of the longer branched chains for more substrates and reagents to be accommodated and to access the catalytic species, and (iii) more catalytic species can be loaded on the unit surface by exchanging with anion of IL.…”

Section: Introductionmentioning

confidence: 99%

“…Our group proved their high efficiency and recyclability for some organic reactions in neat water. 27 Encouraged by our previous research, it was developed a catalytic assembly of dianion peroxotungstates held in bis-layer ionic liquid brushes-modified silica SiO 2 -BisILs[W 2 O 3 (O 2 ) 4 ] (Figure 1). It was envisioned that this catalytic assembly could work well as a green and reusable catalyst in on-water reactions using H 2 O 2 as oxidant.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Ma¹,

Ou²,

Han³

et al. 2012

J. Braz. Chem. Soc.

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Uma sistema catalítico heterogêneo de peroxotungstato realizado em líquido iônico (IL) tipo escova foi sintetizado e aplicado na oxidação seletiva de sulfetos a temperatura ambiente e usando peróxido de hidrogênio 30 wt.% como oxidante terminal e água como solvente. Nenhum cosolvente orgânico ou outro aditivo foi necessário e a reação ocorre com uma quantidade de 1,5-2,0 mol% (baseado no W) de catalisador. Sulfetos alifáticos e aromáticos foram transformados de maneira eficiente e seletiva em seus respectivos sulfóxidos ou sulfonas pelo controle dos equivalentes de peróxido de hidrogênio. Grupos funcionais sensíveis à oxidação, tais como ligações duplas e hidroxila, não foram afetados mesmo com excesso de peróxido de hidrogênio. O catalisador foi recuperado após a reação via filtração e reutilizado pelo menos oito vezes sem perda significativa de atividade.An efficient and reusable heterogeneous catalytic assembly of peroxotungstate held in a ionic liquid (IL) brush was synthesized and an environmentally-friendly procedure was developed for selective oxidation of sulfides at room temperature using 30 wt.% hydrogen peroxide as the terminal oxidant and water as a sole solvent. No organic co-solvent or other additive was needed. A 1.5-2.0 mol% (based on W atom) loading catalyst was found to be sufficient for a smooth and clean reaction. Both aliphatic and aromatic sulfides were efficiently and selectively transformed into their respective sulfoxides or sulfones by simply controlling of equivalents of hydrogen peroxide. In addition to the high catalytic activity, the catalyst exhibits excellent chemoselectivity. Sensitive functional groups, such as double bond and hydroxyl, remained under the oxidation conditions the reaction even with an excess hydrogen peroxide. The catalyst was easily recovered (via simple filtration) and reused at least eight times without a noticeable loss of activity.

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“…27 The exchange between Cl − and PF General procedure for the selective oxidation of sulfides to sulfoxides…”

Section: Synthesis Of Catalystmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Ma¹,

Ou²,

Han³

et al. 2012

J. Braz. Chem. Soc.

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“…负载催化剂的出现为实现催化剂与产物的高效分离和回收提供了可能. 因此, 各国科学家开发了诸如高分子树脂 [13,14] 、硅胶 [15] 、活性碳 [16,17] 以及离子液体 [18] 等多种载体用于钯催化剂的固载化研究, 取得了不错的结果. 然而, 冗长的钯催化剂分离、回收操作(如过滤、萃取等)困扰着这些固载钯催化剂的广泛应用.…”

Section: 催化剂是钯-膦配体络合物unclassified

Magnetic Nanoparticle Supported Imino-pyridine Palladium Catalyzed Suzuki Reactions

Zhang¹,

Li²,

Zhao³

2016

Chin. J. Org. Chem.

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A new magnetic nanoparticle supported palladium catalyst was successfully prepared by attaching palladium acetates to imino-pyridine ligand functionalized silica-coated nano-Fe 3 O 4 . The as-prepared catalyst was characterized by element analysis, FTIR, TEM, XPS and ICP-AES. It was found to be an efficient catalyst for Suzuki reactions in aqueous medium. And the reactions of various aryl bromides with arylboronic acids could be carried out under air and low Pd loading conditions with 83%～98% yields. Moreover, the catalyst could be easily recovered by magnetic separation and reused five times without a significant loss of catalytic activity.

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“…[59] The catalyst was prepared by an anion exchange reaction between silica-immobilized diimidazolium ionic liquid brushes with the sodium salt of Pd-EDTA (Scheme 6). This catalyst has shown great stability in air and excellent reactivity without any phosphine ligands.…”

Section: Suzuki Couplingmentioning

confidence: 99%

Safer and Greener Catalysts – Design of High Performance, Biodegradable and Low Toxicity Ionic Liquids

Gore¹,

Gathergood²

2013

Ionic Liquids - New Aspects for the Future

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PdEDTA Held in an Ionic Liquid Brush as a Highly Efficient and Reusable Catalyst for Suzuki Reactions in Water

Cited by 71 publications

References 11 publications

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Magnetic Nanoparticle Supported Imino-pyridine Palladium Catalyzed Suzuki Reactions

Safer and Greener Catalysts – Design of High Performance, Biodegradable and Low Toxicity Ionic Liquids

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