Palladium supported on triazolyl-functionalized hypercrosslinked polymers as a recyclable catalyst for Suzuki–Miyaura coupling reactions

Liu, Cijie; Zheng, Lijuan; Xiang, Dexuan; Li, Shasha; Xu, Wei; Luo, Qionglin; Shu, You; Ouyang, Yongzhong; Huang, Lin

doi:10.1039/d0ra01190h

Cited by 14 publications

(8 citation statements)

References 69 publications

(8 reference statements)

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“…54 The last example of metal postfunctionalization of a preformed KAP was the reaction of substituted 1,2,3-triazoles and benzene using method-1 with posterior treatment with PdCl 2 (Figure 6g). 55 As expected, the S BET of the HCP-Pd (731 m 2 •g −1 ) was lower than the parent HCP-triazole (794 m 2 • g −1 ), and it was also attributed to the partial filling of the pores with metal. Again, XPS confirms that the coordination and oxidation state of palladium species (+2) with binding energy is negatively shifted by 0.4 eV, which can be attributed to the coordination with triazoles.…”

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

confidence: 67%

“…The last example of metal postfunctionalization of a preformed KAP was the reaction of substituted 1,2,3-triazoles and benzene using method-1 with posterior treatment with PdCl 2 (Figure g) . As expected, the S BET of the HCP-Pd (731 m 2 ·g –1 ) was lower than the parent HCP-triazole (794 m 2 ·g –1 ), and it was also attributed to the partial filling of the pores with metal.…”

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

confidence: 67%

“…HCPs-Pd (entry 16) was a very effective catalyst for this reaction using EtOH as the solvent, with TON values (moles of product)/(moles of Pd) of 1.66 × 10 4 . 55 For Heck reactions, C−C couplings between aryl or vinyl halides and activated alkenes, two phenanthroline and one bipyridine based-catalyst MOPs-Pd-I, Phen-Pd-MOF, and HCPs-bipy-Pd-II were employed using very similar conditions (entries 19−21). MOPs-Pd-I was more efficient since with lower Pd loading and shorter reaction times similar yields were achieved.…”

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

confidence: 99%

“…The porphyrin-based polymer-supported Pd/KAPs(DCM-TPP) (entry 18) was also an effective catalyst in water and can be recovered and reused even for inactive aryl chloride substrates. HCPs-Pd (entry 16) was a very effective catalyst for this reaction using EtOH as the solvent, with TON values (moles of product)/(moles of Pd) of 1.66 × 10 4 …”

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

confidence: 99%

See 3 more Smart Citations

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)supporting

confidence: 67%

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

confidence: 67%

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

confidence: 99%

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

confidence: 99%

See 2 more Smart Citations

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

Valverde‐González

Iglesias

2021

Chem. Mater.

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“…Fortunately, hot filtration test validated that there was an insignificant leaching of the Pd species. PdNP–HCPs can also be prepared by Friedel–Crafts alkylation reaction using 4‐tritylaniline, [ 60 ] substituted 1,2,3‐triazoles, [ 61 ] and 5‐,10‐, 15‐, and 20‐tetraphenylporphyrin [ 62 ] as the monomer and FDA or dichloromethane as the cross‐linker, respectively. And the resulting materials were proven to be a suitable catalyst for promoting Suzuki coupling reaction, and hydrogenation of ammonia borane, nitro compounds, or α,β‐unsaturated aldehydes.…”

Section: Catalytic Applications Of Hypercrosslinked Polymers Construcmentioning

confidence: 99%

Low‐Cost Hypercrosslinked Polymers by Direct Knitting Strategy for Catalytic Applications

Son

et al. 2020

Adv Funct Materials

103

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Direct knitting of nucleophilic arene monomers in the presence of electrophilic cross‐linker, like formaldehyde dimethyl acetal, is proven to be a cost‐effective and versatile method for the synthesis of porous organic polymers. The resulting hypercrosslinked polymers (HCPs) are featured by hierarchical porous structure, high surface area, and pore volume. Coordinating functional groups can be easily installed with this method into the rigid aryl network. Direct knitting to HCPs has therefore been widely used in preparing heterogeneous solid catalysts. Wise selection of monomers with rational design of 3D structure and the synergy between the HCP support and the catalytically active species often lead to high efficiency of tailor‐made catalysts without sophisticated operations. On account of all these excellent properties, enthusiasm of researchers to use HCPs in catalysis is increasing rapidly. This review documents the necessity, feasibility, and the great contributions of using HCPs as invaluable tools for catalysis research, and summarizes state of the art of this chemistry. Similar type catalysts obtained by one‐step Scholl reaction are also included in this review.

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Palladium catalyst immobilized on functionalized hyper–cross-linked polymers with 8-hydroxyquinoline as monomer for Suzuki–Miyaura coupling reactions

Feng,

Lu,

Zou

et al. 2024

Res Chem Intermed

Self Cite

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An e cient and stable palladium species catalyst immobilized on functionalised hyper-crosslinked polymers (HCPs-Pd) has been successfully developed and applied in the Suzuki-Miyaura coupling reaction of diverse types of aromatic halides with aromatic boric acid in this work. The results demonstrated that HCPs-Pd exhibited high catalytic activity, which bene ted from the microporous structure of the catalyst guaranteed high dispersibility of active palladium, and high speci c surface area, large pore volume, good chemical stability. Under optimal reaction conditions, 93.0% of biphenyl yield in the Suzuki-Miyaura reaction with bromobenzene (C 6 H 5 Br) and phenylboric acid (C 6 H 7 BO 2 ) as raw material was obtained. The good stability of the HCPs-Pd catalyst was veri ed by ve cycles experiments. Perhaps this work provides new insights into the high-yield preparation of biphenyl aromatic compounds employing HCPs-Pd as an e cient and stable catalyst in the Suzuki-Miyaura reaction.

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Palladium supported on triazolyl-functionalized hypercrosslinked polymers as a recyclable catalyst for Suzuki–Miyaura coupling reactions

Abstract: A novel hypercrosslinked polymer-palladium catalyst was prepared via external cross-linking reactions and applied in Suzuki–Miyaura reactions as a recyclable catalyst, resulting in TON numbers up to 1.66 × 104 and yields reaching 99%.

Cited by 14 publications

References 69 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

Low‐Cost Hypercrosslinked Polymers by Direct Knitting Strategy for Catalytic Applications

Palladium catalyst immobilized on functionalized hyper–cross-linked polymers with 8-hydroxyquinoline as monomer for Suzuki–Miyaura coupling reactions

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