Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation

Lei, Yizhu; Zhang, Xuefeng; Gu, Yanlong; Hu, Jianglin; Li, Guangxing; Shi, Kaiyi

doi:10.1007/s11243-015-9990-6

Cited by 19 publications

(11 citation statements)

References 34 publications

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“…It is also indicated that previous results relied on very high pressure (5–20 bar) of CO in the absence of a CO absorbent (Table S4, Supporting Information). 37‐40 Thus, the reactive absorption of CO by [BimH]Cl‐CuCl‐1.0ZnCl 2 can dramatically decrease the pressure and efficiently promote carbonylation reaction to obtain 70–97 yields.…”

Section: Resultsmentioning

confidence: 99%

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Tao

et al. 2020

AIChE Journal

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Achieving efficient dissolution of carbon monoxide (CO) in the solvent is very helpful for the implementation of carbonylation reaction at ambient pressure. However, almost all of common solvents show very low solubilities of CO at high temperature. Herein, a series of cuprous‐based ternary deep eutectic solvent (DES) was prepared by mixing imidazolium hydrochloride with CuCl and ZnCl2. The ternary DES [BimH]Cl‐CuCl‐1.0ZnCl2 exhibited very large CO absorption capacity (0.075 mol mol−1, 1 bar) even at a high temperature (353.2 K), which is superior to all of the reported absorbents. Moreover, the ternary DES [BimH]Cl‐CuCl‐1.0ZnCl2 could further promote the reactive absorption of CO to conduct the aminocarbonylation reaction effortlessly at ambient pressure, and thus the targeted products benzamides were obtained in 70–97 yields. We believe that this finding opens a new way to design advanced solvents for efficient capture of CO at high temperature.

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Section: Resultsmentioning

confidence: 99%

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Tao

et al. 2020

AIChE Journal

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“…Lei et al reported also the same catalyst in the synthesis of aryl amides by aminocarbonylation of aryl iodides. 41 Triphenylphosphine (PPh 3 ) has been also knitted with 1,3,5-triphenylbenzene (sym-PhPh 3 ) following method-2 and then reacted with PdCl 2 to yield the catalysts SMP-8b (Figure 6a) used also in Suzuki−Miyaura coupling reactions. 42 The second type of functional building monomers reported to coordinate Pd is N-heterocyclic carbenes (NHCs), electronrich nucleophilic ligands that make strong organometallic bonds with metals.…”

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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“…The purity of products was checked by NMR and yields were based on aryl iodides. All the synthesized amides are known products and have been reported recently …”

Section: Methodsmentioning

confidence: 99%

“…In continuation of our studies of the synthesis of amides via catalytic aminocarbonylation reactions, we herein report the carbonylation of aryl halides with various nucleophilic reagents (amines, NH 3 , alcohols, water) under mild reaction conditions. Under mild reaction temperature, an efficient approach for synthesizing aryl amides by aminocarbonylation of aryl halides with alicyclic amines is described.…”

Section: Introductionmentioning

confidence: 99%

Mild and efficient Pd(P^tBu₃)₂‐catalyzed aminocarbonylation of aryl halides to aryl amides with high selectivity

Lei

Xiao

et al. 2016

Applied Organom Chemis

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This work describes a mild and efficient approach for the synthesis of aryl amides via catalytic aminocarbonylation of aryl halides with alicyclic amines using a Pd (P t Bu 3 ) 2 /NH 4 Cl catalyst system. Under mild reaction temperature of 60°C and balloon pressure of CO, 5 mol% Pd(P t Bu 3 ) 2 with a cheap NH 4 Cl promoter is sufficient for high yields of aryl amides. The influence of reaction parameters such as reaction temperature, ligand type and promoter on catalytic activity was investigated. This work also discusses the catalytic intermediates in detail, and provides a plausible mechanism based on an acid chloride intermediate.

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Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation

Cited by 19 publications

References 34 publications

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

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

Mild and efficient Pd(P^tBu₃)₂‐catalyzed aminocarbonylation of aryl halides to aryl amides with high selectivity

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Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation

Cited by 19 publications

References 34 publications

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

Promoted absorption of CO at high temperature by cuprous‐based ternary deep eutectic solvents

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

Mild and efficient Pd(PtBu3)2‐catalyzed aminocarbonylation of aryl halides to aryl amides with high selectivity

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Mild and efficient Pd(P^tBu₃)₂‐catalyzed aminocarbonylation of aryl halides to aryl amides with high selectivity