A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C–N coupling reaction

Gorginpour, Forough; Zali‐Boeini, Hassan; Rudbari, Hadi Amiri

doi:10.1039/d0ra10741g

Cited by 14 publications

(8 citation statements)

References 77 publications

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“…The known compound 4 has been also prepared from the reaction of NaCN with 2 for 48-64 h stirring at room temperature under inert atmosphere. [37][38][39] The synthesis routes are drawn in Schemes S1-S3. All products were characterized by NMR measurements which are identical to those of the reported data (Figs.…”

Section: Resultsmentioning

confidence: 99%

Optical Sensing and Supramolecular Cyanide Recognition Sites of Salophenes as Molecular Tweezers: The First Example of Recognition via Intramolecular Aldimine Condensation Cyclization

Darabi

Nazarian

Alizadeh

et al. 2021

Preprint

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The optical sensing and supramolecular cyanide recognition sites of two dipodal Schiff bases having conjugated to catecols (1) and phenols (2) (namely, salophenes 1 and 2) have been studied. In the case of optical sensing, both probes recognized only cyanide (CN¯) ions in 30% PBS buffer CH3CN (pH 7.4) as confirmed from the changes of absorption and emission bands, resulting in color changes. From the supramolecular recognition point of view, probes 1 and 2 show the different recognition bahaviour toward CN¯, as evidenced by the fluoroscence and NMR data, as well the OH¯ and reversibility experiments. While 1 recognizes CN¯ via deprotonation, that of 2 is the first example of Schiff base which senses CN¯ through an intramolecular aldimine condensation cyclization, leading to formation of dihydroxyquinoxaline 4. In general, probes 1, 2 and 4 are promising on-site optical sensors in terms of easy prepared, selectivity, sensitivity (1–10 nM), ease of use, rapid response (< 5 s) and test kits.

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Section: Resultsmentioning

confidence: 99%

Optical Sensing and Supramolecular Cyanide Recognition Sites of Salophenes as Molecular Tweezers: The First Example of Recognition via Intramolecular Aldimine Condensation Cyclization

Darabi

Nazarian

Alizadeh

et al. 2021

Preprint

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“…Aryl halides (except aryl fluorides) were successfully coupled with aromatic amines via Ullmann C−N coupling using Cu nanoparticles loaded quinoxaline‐based POPs (Scheme 6). [37] Diarylamines were produced in good to excellent yields. Aryl iodides showed higher reactivity compared to aryl bromides and aryl chlorides.…”

Section: C‐n Coupling Reactionmentioning

confidence: 99%

Metal‐Ion/Metal Nanoparticle‐Anchored Porous Organic Polymers as Efficient Catalysts for Organic Transformations – A Recent Overview

Kathiresan

2023

Chemistry An Asian Journal

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Porous organic polymers are porous materials that are interlinked with organic building blocks by strong covalent bonds. The functional groups on the building blocks can be carefully chosen to obtain a POP with desired functionalities. In certain cases, the pores or voids interact with the organic molecules via non‐covalent interactions and hence they serve as catalytic centers. In many cases, pristine POPs themselves were evaluated as heterogeneous catalysts for their catalytic activity. The inner functional groups of POPs act as a ligand or interact with metal ions/metal nanoparticles and hence a wide range of metal‐ion‐anchored POPs or metal nanoparticle‐loaded POPs were reported. These metal‐ion‐anchored POPs can catalyze different organic reactions as that of pristine metal‐based catalysis following a heterogeneous pathway. In this type of catalysis, POP plays an important role, i. e., it serves as a carbon matrix, and interacts with organic molecules via non‐covalent interactions, further in metal/metal‐ion‐anchored POPs, the metal concentration is highly reduced and the organic transformation effectively takes place at the interface of metal/carbon matrix. Herein, we discuss the recent developments on metal‐ion/metal nanoparticle loaded POPs and their role in various organic transformations such as C−C coupling reactions, borrowing hydrogen reactions, CO2 transformations, hydroformylations reactions, oxidation of alkynes to 1,2‐diketones and C−H arylation reactions.

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“…In a very recent study, Zali‐Boeini and co‐workers [ 201 ] disclosed the use of a novel porous organic polymer (Q‐POP) as an ideal support for immobilizing copper NPs. The CuNPs@Q‐POP nanocatalyst was fabricated through free‐radical copolymerization of allyl‐substituted 2,3‐di(2‐hydroxyphenyl)1,2‐dihydroquinoxaline and divinylbenzene in the presence of azobisisobutyronitrile (AIBN) as the radical initiator using a solvothermal method, followed by the incorporation of Cu (NO 3 ) 2 into the polymeric network and subsequent addition of hydrazine hydrate as a reducing agent.…”

Section: Copper Nanocatalystsmentioning

confidence: 99%

Recent advances in the application of nanocatalysts in C‐N coupling reactions

Rangraz

Heravi

2022

Applied Organom Chemis

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The development of various methodologies for the formation of carbon‐nitrogen bonds is one of the valuable tasks in the field of organic synthesis because the final products are extensively utilized in pharmaceuticals, biologically active compounds, and natural products. The utilization of nanosized metal catalysts with high surface energy, large surface‐to‐volume ratio, excellent thermal stability, and reactive morphology in C‐N cross‐coupling reactions has received considerable attention, in recent years. The excellent catalytic performance, the high yield of products, carrying out the reactions under relatively mild and ligand‐free conditions, and less toxicity to the environment, recoverability, and reusability of catalysts for several times without a remarkable degradation in activity are advantages of these nanocatalysts. This review intends to summarize the latest progress in the fabrication of nanocatalysts and their applications in the construction of carbon‐nitrogen bonds via cross‐coupling reactions. Abundant nanocatalysts based on metal and metal oxide nanoparticles/complexes including copper, palladium, nickel, cobalt, silver, gold, zirconium, and zinc have successfully been applied in these reactions. Various aspects of the reactions, different strategies of fabrication of nanocatalysts, and their recyclability have been surveyed. Literature has been investigated from 2015 to 2021.

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A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C–N coupling reaction

Abstract: A novel efficient catalyst for the Ullmann C–N coupling reaction has been developed.

Cited by 14 publications

References 77 publications

Optical Sensing and Supramolecular Cyanide Recognition Sites of Salophenes as Molecular Tweezers: The First Example of Recognition via Intramolecular Aldimine Condensation Cyclization

Optical Sensing and Supramolecular Cyanide Recognition Sites of Salophenes as Molecular Tweezers: The First Example of Recognition via Intramolecular Aldimine Condensation Cyclization

Metal‐Ion/Metal Nanoparticle‐Anchored Porous Organic Polymers as Efficient Catalysts for Organic Transformations – A Recent Overview

Recent advances in the application of nanocatalysts in C‐N coupling reactions

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