Palladium Immobilized on 2,2′-Dipyridyl-Based Hypercrosslinked Polymers as a Heterogeneous Catalyst for Suzuki–Miyaura Reaction and Heck Reaction

Liu, Cijie; Xu, Wei; Xiang, Dexuan; Luo, Qionglin; Zeng, Shunqin; Zheng, Lijuan; Tan, Yu-Jie; Ouyang, Yongzhong; Huang, Lin

doi:10.1007/s10562-020-03165-4

Cited by 14 publications

(8 citation statements)

References 46 publications

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“…1,10-Phenanthroline, 4,7-diphenyl-1,10-phenanthroline, and 2,2′-bipyridine are other interesting types of bidentate building monomers to prepare palladium-based KAPs because of the proximity of their two nitrogen atoms, which provide excellent binding sites. Thus, Xu et al, 47 Wang et al 48 and Liu et al 49 have recently reported the heterogeneous catalysts, MOP-I-Pd, MOP-II-Pd, Phen-MOP-Pd, HCPs-bipy−-Pd-I, and HCPsbipy−Pd-II (Figure 6c), containing these kinds of units, by reacting the corresponding precursor supports with PdCl 2 or Pd(OAc) 2 . These supports were prepared from 1,10phenanthroline, 4,7-diphenyl-1,10-phenanthroline, or 2,2′bipyridine and benzene as comonomer using method-1 (for POP-I and HCPs-bipy-I) and method-2 for the rest of the networks.…”

Section: Metal Complexes On Knitting Aryl Polymers (Kap-m)mentioning

confidence: 99%

Metal Catalysis with Knitting Aryl Polymers: Design, Catalytic Applications, and Future Trends

Valverde‐González

Iglesias

2021

Chem. Mater.

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In 2011, a new type of hyper-cross-linked polymers (HCPs) arose, known as knitting aromatic polymers (KAPs), characterized by their extraordinary chemical and thermal stability, by their porosity properties, and above all, for the simplicity of their synthesis based on the union of aromatic monomers, without any previous functionalization. The next logical step was the incorporation of metals within these networks, as support for different soluble molecular catalysts or metal nanoparticles (NPs). Thus, the number of metal-containing KAPs has been gradually growing in the past decade, and we have considered that now, in the 10th anniversary of the first KAPs reported, a review of all the metal-containing KAPs and their application as heterogeneous metal catalysts is mandatory. In this review, the most relevant characteristics of all KAPs that contain metals are summarized, divided into two large groups, either as metal complexes or as metal NPs, and classified according to the type of metal incorporated. Finally, the catalytic activities were compared based on the metal employed in each studied reaction, and the future goals of these types of materials are commented on.

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Section: Metal Complexes On Knitting Aryl Polymers (Kap-m)mentioning

confidence: 99%

Metal Catalysis with Knitting Aryl Polymers: Design, Catalytic Applications, and Future Trends

Valverde‐González

Iglesias

2021

Chem. Mater.

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“…In the more concentrated condition, formation of inactive Pd(0) particles was observed, leading to poor recyclability. On the other hand, at the denoted "dilute condition", such particles Xu 2020 [71] Phenanthroline-based microporous organic polymer Several/AlCl…”

Section: Discussionmentioning

confidence: 99%

An Imidazole‐Rich Pd(II)‐Polymer Pre‐catalyst for the Suzuki‐Miyaura Coupling: Stability Influenced by Dissolved Oxygen and Reactants Concentration

et al. 2022

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Herein a novel Pd(II)-polymeric pre-catalyst was prepared by coordinating Pd(II) ions to a low cost imidazole/carboxylate-rich polymer. The material displays good activity in the Suzuki-Miyaura coupling towards a range of aryl bromides and iodides in iPrOH/H 2 O mixtures at 25 or 60 °C. Catalyst longevity and recyclability proved to be sensitive to the concentration of the cross-coupling partners. When the concentration of PhBr is high ([PhBr] = 250 mmol L À 1 ), inactive Pd(0) aggregates were de-tected. On the other hand, when the reaction was performed at 20-fold dilution ([PhBr] = 12.5 mmol L À 1 ) the material could be reused up to 12 times without significant loss of catalytic activity. In this condition, minimum amount of Pd(0) was detected by XPS analysis and no Pd(0) aggregates were observed by XRPD. Importantly, it was found that the presence of oxygen is fundamental for avoiding formation of inactive Pd(0) aggregates.[a] E.

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“…Organic base like Et 3 N was very less effect in reaction protocol and 35 % of 10 a was formed (Table 3, entry 10). Screening of other solvent also reveals that solvent other than water gave lower yield of the product 10 a (Table 3, entries [11][12][13][14][15][16][17][18][19][20]. Moreover the use of other palladium salt like Pd(OAc) 2 and Pd(OTf) 2 remarkably decreased the yield of product 10 a yield (Table 3, entries 21,22).…”

Section: Mizoroki-heck Reaction Reactionmentioning

confidence: 97%

“…[11] Thus, chemists have tried to synthesize new sterically crowded phosphines free ligand and tried to use in the coupling reaction as ligand. In contrast to the other ligands the low toxicity and high stability of O-, N-based ligands like aryloximes or O-aryloxime ether, [12] N-acylamidines, [13] N-heterocyclic carbenes, [14] simple amines, [15] pyridine-piperidine, [16] bipyridine, [17] and phenanthroline [18] are effective ligands in the Suzuki-Miyaura and Mizoroki-Heck coupling reactions. These ligands are thermally stable, and are well-known for their great tenability by varying substituents on the donor atoms, and they can be bind to central metal atom in either the ionic state or neutral state.…”

Section: Introductionmentioning

confidence: 99%

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

Khan

Parveen

2021

Eur J Org Chem

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A new family of phosphine-free Amino-chroman-4-one ((Z)-2ethoxy-3-((phenylamino)methylene)chroman-4-one) bidentate ligands ware successfully synthesised and characterised. The bidentate ligand act as efficient catalyst with combination of Pd (II) salt in the CÀ C bond formation and exhibited excellent performance in the Suzuki-Miyaura and Mizoroki-Heck coupling reaction. A broad range of substrates, including heterocyclic, flavones, Isatin and sterically hindered coupling partner, were well tolerated under the optimized reaction conditions. Metal complex and all the intermediates were formed in the catalytic cycle were characterized by mass spectrometry to support the reaction mechanism.

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Palladium Immobilized on 2,2′-Dipyridyl-Based Hypercrosslinked Polymers as a Heterogeneous Catalyst for Suzuki–Miyaura Reaction and Heck Reaction

Cited by 14 publications

References 46 publications

Metal Catalysis with Knitting Aryl Polymers: Design, Catalytic Applications, and Future Trends

Metal Catalysis with Knitting Aryl Polymers: Design, Catalytic Applications, and Future Trends

An Imidazole‐Rich Pd(II)‐Polymer Pre‐catalyst for the Suzuki‐Miyaura Coupling: Stability Influenced by Dissolved Oxygen and Reactants Concentration

Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium

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