CuO/Fe2O3 NPs: robust and magnetically recoverable nanocatalyst for decarboxylative A3 and KA2 coupling reactions under neat conditions

Gulati, Upasana; Rajesh, U. Chinna; Rawat, Diwan S.

doi:10.1016/j.tetlet.2016.08.066

Cited by 45 publications

(24 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the same year, Rawat and co‐workers reported a novel synthetic route for the preparation of the CuO/Fe 2 O 3 NPs as a green, sustainable and magnetically recoverable nanocatalyst . For the first time, the catalytic activity of the CuO/Fe 2 O 3 successfully was studied for the synthesis of trisubstituted and tetrasubstituted propargylamines via decarboxylative A 3 and KA 2 coupling reactions, respectively (Scheme ).…”

Section: The Various Catalytic Systems For A3 Coupling Reactionsmentioning

confidence: 99%

“…It is important to stress that despite huge advancements of the reported works in the literature, another important challenges in the A 3 coupling reactions is nature of solvent and kind of the catalyst. A number of nanocatalysts, including copper, silver, gold, nickel, magnetic nanocatalysts and Co 3 O 4 , ZnS and nanopowder zinc titanate were successfully applied for A 3 coupling reactions with yields ranging from good to excellent in appropriate times in organic solvents or aqueous medium . The authors ascribed high catalytic activity of nanocatalysts to the particles size.…”

Section: Outlook and Conclusionmentioning

confidence: 99%

See 1 more Smart Citation

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Nasrollahzadeh

Sajjadi

Ghorbannezhad

et al. 2018

The Chemical Record

View full text Add to dashboard Cite

A coupling is one of the few transition-metal catalyzed carbon-carbon bond forming reactions that have been established as a most direct, efficient and atom-economical synthetic approach to afford propargylamine derivatives using various catalysts. A large number of nanosized heterogeneous catalysts for three-component coupling reactions between an aldehyde, an amine, and a terminal alkyne have been popularly introduced as an A coupling in the last decade. The coupling product has found a broad application as a key intermediate for a variety of heterocyclic useful compounds and numerous biologically active molecules such as β-lactams, conformationally restricted peptides, isosteres, herbicides, fungicides, indolizines, pyrroles, quinolines and therapeutic drug molecules. This review aims to give an overview of the current progress made towards the preparation and application of various nanocatalysts-catalyzed A coupling transformations for the synthesis of propargylamines from 2007 to 2017. Several nanocatalysts based on metal and metal oxide nanoparticles (NPs) such as copper, gold, silver, iron, nickel, cobalt and zinc have successfully been employed in A coupling reactions. Besides, core-shells NPs, polymers, complexes, graphenes, metal-organic frameworks and ionic liquids have also been used in these reactions. Abundant examples have been given in this area. Different aspects of the reactions, disparate methods of preparation of nanocatalysts, characterization and their reusability have been perused.

show abstract

Section: The Various Catalytic Systems For A3 Coupling Reactionsmentioning

confidence: 99%

Section: Outlook and Conclusionmentioning

confidence: 99%

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Nasrollahzadeh

Sajjadi

Ghorbannezhad

et al. 2018

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…Examples of homogeneous catalysts which have been employed include CuI, CuBr, Cu (OTf) 2 , AuBr 3 , CuCl 2 /Ti(OEt) 4. The representative heterogeneous catalysts covered Amberlyst A‐21 supported CuI, CuNPs@ZnO–PTh, CuO/Fe 2 O 3 NPs, nano Cu 2 O–ZnO . No matter A 3 or KA 2 couplings, a terminal alkyne is a common reactant partner which occasionally produces the Glaser‐Hay homocoupling by‐product in the presence of some kind of metal catalytic systems resulting in decreasing the yield of the propargylamine product .…”

Section: Introductionmentioning

confidence: 99%

“…In the decarboxylative A 3 couplings, alkynyl carboxylic acids act as economical and stable surrogate for terminal alkynes via extrusion of CO 2 in situ. Thus, a number of homogeneous catalysts such as CuI, CuBr, CuCl 2 /CuI, CuI/Cu(OTf) 2 , and heterogeneous catalysts including Cu(II)/HM, CuO/Fe 2 O 3 NPs, Cu@SiO 2 ‐NS, and chit@copper have been used in decarboxylative A 3 coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Cu^II@PAA/PVC mesoporous fibers: A hybrid wedding as a high‐performance versatile heterogeneous catalyst for A₃, KA₂, and decarboxylative A₃ reactions

Jiang

Zhou

Sun

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

Efforts made on the development of a novel, simple, cost‐effective, and efficient approach to fabricate a copper catalyst immobilized on mesoporous poly (acrylic acid)/poly (vinyl chloride) hybrid fibers (CuII@PAA/PVC) for versatile catalytic applications in A3, KA2, and decarboxylative A3 couplings has been described in this present work. The characterization of the mesoporous hybrid fibers was well performed by BET, FTIR, SEM, EDX, XPS, and TGA techniques. The pore structure and surface area were calculated by using BET measurement analysis. The obtained mesoporous CuII@PAA/PVC fibers exert high catalytic performance in the synthesis of propargylamines via one‐pot A3, KA2, and decarboxylative A3 reactions over a series of substrates without employing expensive ligands or inert atmosphere. The active Cu2+ species chelating with carboxylate groups in PAA/PVC hybrid fibers plays a key role in the catalysis. Meanwhile, the unique mesoporous structure and fiber morphology facilitate a better mass transfer and enlarge its contact area with substrates in the course of a reaction. Moreover, the Cu2+–carboxylate chelation could suppress the leaching of active Cu2+ species from the catalyst and thus lead to the catalyst has excellent performance and good durability as well as reusability.

show abstract

“…Recently, different homogenous catalysts such as CuCl, CuBr, CuI, Cu (I) PF 6 ‐ligand, CuCl 2 , Fe‐I 2 ‐CuBr, and Cu (I) pybox complex have been successfully used for the synthesis of propargylamine. However, to overcome disadvantages associated with homogenous catalysts such as poor recycling, stability, and handling in high scale industrial synthesis of propargylamine, heterogeneous catalysts have also been designed . They too consistently suffer from several problems such as sintering and Ostwald ripening.…”

Section: Introductionmentioning

confidence: 99%

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

View full text Add to dashboard Cite

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%).

show abstract

CuO/Fe2O3 NPs: robust and magnetically recoverable nanocatalyst for decarboxylative A3 and KA2 coupling reactions under neat conditions

Cited by 45 publications

References 28 publications

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Cu^II@PAA/PVC mesoporous fibers: A hybrid wedding as a high‐performance versatile heterogeneous catalyst for A₃, KA₂, and decarboxylative A₃ reactions

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

Contact Info

Product

Resources

About

CuO/Fe2O3 NPs: robust and magnetically recoverable nanocatalyst for decarboxylative A3 and KA2 coupling reactions under neat conditions

Cited by 45 publications

References 28 publications

A Review on Recent Advances in the Application of Nanocatalysts in A3 Coupling Reactions

A Review on Recent Advances in the Application of Nanocatalysts in A3 Coupling Reactions

CuII@PAA/PVC mesoporous fibers: A hybrid wedding as a high‐performance versatile heterogeneous catalyst for A3, KA2, and decarboxylative A3 reactions

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

Contact Info

Product

Resources

About

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Cu^II@PAA/PVC mesoporous fibers: A hybrid wedding as a high‐performance versatile heterogeneous catalyst for A₃, KA₂, and decarboxylative A₃ reactions