Nitro resin supported copper nanoparticles: An effective heterogeneous catalyst for C N cross coupling and oxidative C C homocoupling

Barot, Nirav; Patel, Saumya; Kaur, Harjinder

doi:10.1016/j.molcata.2016.06.009

Cited by 31 publications

(17 citation statements)

References 51 publications

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“…It is estimated that only a few hundred tons of the total production were converted to Cu-based nanoparticles (Cu NPs) , despite there being many emerging applications for nano-Cu materials. Many applications involve the traditional role of Cu as a conductor, such as conductive dyes (Albrecht et al, 2016;Hokita et al, 2015;Tam and Ng, 2015;Kharisov and Kharissova, 2010;Tsai et al, 2015;Gopalan et al, 2016) or heat transfer fluids (Park et al, 2015;Montes et al, 2015;Azizi et al, 2016;Rizwan-ul-Haq et al, 2016), but the use of nano-Cu is rapidly expanding into novel applications such as catalysts in organic synthesis (Dugal and Mascarenhas, 2015;Lennox et al, 2016;Barot et al, 2016), sensors (Albrecht et al, 2016;Tsai et al, 2015;Gopalan et al, 2016;Brahman et al, 2016;Pourbeyram and Mehdizadeh, 2016), solar cells (Yoon et al, 2010;Parveen et al, 2016;Shen et al, 2016), light-emitting diodes , hydrogen generation (Liu et al, 2015a;Liu et al, 2015b), and drug delivery (Woźniak-Budych et al, 2016). Based on the antifungal and antimicrobial properties of Cu + 2 , Cu NPs are actively being developed for applications in agriculture and food preservation (Park et al, 2015;Montes et al, 2015;Dugal and Mascarenhas, 2015;Ray et al, 2015;Kalatehjari et al, 2015;Ponmurugan et al, 2016;Maniprasad et al, 2015;Majumder and Neogi, 2016;Villanueva et al, 2016), textiles …”

Section: Introductionmentioning

confidence: 99%

Comparative environmental fate and toxicity of copper nanomaterials

et al. 2017

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A B S T R A C TGiven increasing use of copper-based nanomaterials, particularly in applications with direct release, it is imperative to understand their human and ecological risks. A comprehensive and systematic approach was used to determine toxicity and fate of several Cu nanoparticles (Cu NPs). When used as pesticides in agriculture, Cu NPs effectively control pests. However, even at low (5-20 mg Cu/plant) doses, there are metabolic effects due to the accumulation of Cu and generation of reactive oxygen species (ROS). Embedded in antifouling paints, Cu NPs are released as dissolved Cu + 2 and in nano-and micron-scale particles. Once released, Cu NPs can rapidly (hours to weeks) oxidize, dissolve, and form CuS and other insoluble Cu compounds, depending on water chemistry (e.g. salinity, alkalinity, organic matter content, presence of sulfide and other complexing ions). More than 95% of Cu released into the environment will enter soil and aquatic sediments, where it may accumulate to potentially toxic levels (> 50-500 μg/L). Toxicity of Cu compounds was generally ranked by high throughput assays as: Cu + 2 > nano Cu(0) > nano Cu(OH) 2 > nano CuO > micron-scale Cu compounds. In addition to ROS generation, Cu NPs can damage DNA plasmids and affect embryo hatching enzymes. Toxic effects are observed at much lower concentrations for aquatic organisms, particularly freshwater daphnids and marine amphipods, than for terrestrial organisms. This knowledge will serve to predict environmental risks, assess impacts, and develop approaches to mitigate harm while promoting beneficial uses of Cu NPs.

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Section: Introductionmentioning

confidence: 99%

Comparative environmental fate and toxicity of copper nanomaterials

et al. 2017

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“…In addition, the metal nanoparticles are highly stabilized in the polystyrene resin because of the electrostatic stabilization and steric stabilization. Supporting copper nanoparticles on polystyrene resin beads was performed in a 2‐step process reported earlier by our group . High‐resolution transmission electron microscopy (TEM) images indicated that the copper nanoparticles present in the interior of polymeric matrix of the polystyrene resin were of 3 to 9 nm dimension (Figure A).…”

Section: Resultsmentioning

confidence: 95%

“…Nevertheless, the issues of recyclability again reduced the adaptability of this catalyst . In our recent report, we reported the synthesis and characterization of copper nanoparticles stabilized onto a novel nitro functionalized polystyrene resin (Cu NPs@ Nitro functionalized Resin) and investigated its catalytic activity towards the C–N coupling of various aromatic amines with aryl halides and the oxidative C–C homocoupling of phenyacetylene . In the present investigation, we studied the feasibility and sustainability of this catalyst for the synthesis of propargylamine under microwave heating.…”

Section: Introductionmentioning

confidence: 99%

“…[47] In our recent report, we reported the synthesis and characterization of copper nanoparticles stabilized onto a novel nitro functionalized polystyrene resin (Cu NPs@ Nitro functionalized Resin) and investigated its catalytic activity towards the C-N coupling of various aromatic amines with aryl halides and the oxidative C-C homocoupling of phenyacetylene. [48] In the present investigation, we studied the feasibility and sustainability of this catalyst for the synthesis of propargylamine under microwave heating. The effect of various reaction parameters such as solvent, temperature, reaction time, catalyst quantity, etc was studied on the yield of products.…”

Section: Introductionmentioning

confidence: 99%

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Microwave‐assisted facile synthesis of propargylamine library by robust nitro functionalized cross‐linked polystyrene resin supported Cu NPs

Sharma

Kaur

Barot

2017

J of Physical Organic Chem

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In the present investigation, we study catalytic activity of copper nanoparticles stabilized onto a nitro functionalized polystyrene resin (Cu NPs@ Nitro-Resin).The size of stabilized copper nanoparticles was found between 3 and 9 nm. This work reports a cost-effective and sustainable protocol for the synthesis of propargylamines. Herein, we have developed microwave-assisted synthesis of propargylamine from 3 components coupling of aldehyde, alkynes, and amines (A 3 coupling) in truly heterogeneous catalytic system. Reaction parameters, such as solvent, catalyst concentration reaction time, and recyclability, were investigated, and reaction conditions were optimized. The present method has advantages such as environmentally benign, ease to handle, short reaction time (≈25 min), excellent yields (98%), low E-factor (0.15), and high atom economy (94%).

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“…However, there are very less reports of nanoparticles as catalysts in this oxidative coupling reaction . This reaction was earlier reported by our group with copper nanoparticles supported on nitro functionalized polystyrene resin but one drawback was there it requires much more time to complete the reaction. Therefore, we decided to explore this reaction under microwave by using the same optimized reaction condition by adding base and oxygen as a terminal oxidant.…”

Section: Synthesis Of Propargylaminesmentioning

confidence: 97%

Carbon Nitride‐Supported Silver Nanoparticles: Microwave‐ Assisted Synthesis of Propargylamine and Oxidative C‐C Coupling Reaction

Patel

Vasava

2018

ChemistrySelect

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In the present study we have, synthesized silver nanoparticles supported on carbon nitride AgNPs@g‐C3N4 and investigated its catalytic aspects by using microwave. We found that silver nanoparticles supported on g‐C3N4 were highly active in the A3‐coupling reaction of (Aldehyde, secondary amine and terminal alkynes) for the synthesis of propargylamines with excellent yield up to 97% and in C−C coupling reaction of terminal alkynes for the synthesis of 1, 3‐diyne with excellent yield up to 98%. We have achieved excellent TON (72932), TOF (3636 min−1), E‐factor (0.27) and atom economy AE (94%). Reaction parameters like effect of catalyst quantity, effect of time and effect of temperature was deeply studied. The catalyst was characterized by SEM, HR‐TEM, EDX, XRD, ICP‐AES and IR.

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Nitro resin supported copper nanoparticles: An effective heterogeneous catalyst for C N cross coupling and oxidative C C homocoupling

Cited by 31 publications

References 51 publications

Comparative environmental fate and toxicity of copper nanomaterials

Comparative environmental fate and toxicity of copper nanomaterials

Microwave‐assisted facile synthesis of propargylamine library by robust nitro functionalized cross‐linked polystyrene resin supported Cu NPs

Carbon Nitride‐Supported Silver Nanoparticles: Microwave‐ Assisted Synthesis of Propargylamine and Oxidative C‐C Coupling Reaction

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