Amino acid ionic liquid bound copper Schiff base catalyzed highly efficient three component A3-coupling reaction

Varyani, Manish; Khatri, Praveen K.; Jain, Suman L.

doi:10.1016/j.catcom.2016.01.020

Cited by 41 publications

(13 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It also seems to be comparable with the activity of the homogenous catalytic systems described in Ref. for the same A 3 coupling reaction. Furthermore, similarly to some catalysts developed by other groups, catalyst 3‐Cu could be used successfully several times.…”

Section: Resultssupporting

confidence: 84%

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Bukowska

Bukowski

Bester

et al. 2017

Applied Organom Chemis

View full text Add to dashboard Cite

New polymer supported Cu(II) complexes based on an epoxy functionalized gel type resin were prepared using the multi-stage procedures. The reactions of epoxy groups with ethylenediamine or tris(2-aminoethyl)amine, and then NH 2 groups with salicylaldehydes were used for the preparation of a series of amine-imine functionalized polymer supports. Copper(II) acetate was used as a source of metal ions. The complexes were characterized using ICP-OES, FTIR, DR UV-Vis and TGA techniques, and tested as catalysts in two model C-N and a series of A 3 coupling reactions. Their catalytic activity was rather low in the C-N coupling reactions between imidazole and iodobenzene or phenylboronic acid. However, the second of the reactions could be conducted effectively under milder conditions. The complexes were efficient used as recyclable catalysts in the A 3 coupling reactions.A series of aromatic aldehydes and secondary amines and phenylacetylene could be coupled using 1% mol catalyst.

show abstract

Section: Resultssupporting

confidence: 84%

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Bukowska

Bukowski

Bester

et al. 2017

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Propargylamines exhibit biological properties, such as anti-Alzheimer, anti-Parkinsonian, and antidepressant activities 3–5 . Methods used to prepare propargylamines include amination of propargylic electrophiles 6 , nucleophilic addition of alkynes to imines or enamines 7 , and three-component (aldehyde, terminal alkyne, and amine, A 3 ) coupling reactions through C–H activation 8,9 . Among these synthetic strategies, A 3 coupling is the most efficient, and it permits construction of complex structures from simple starting materials with water as byproduct 10,11 .…”

Section: Introductionmentioning

confidence: 99%

“…Among these synthetic strategies, A 3 coupling is the most efficient, and it permits construction of complex structures from simple starting materials with water as byproduct 10,11 . In recent years, various metals such as Au 9 , Cu 8 , Ag 12 , In 13 , Fe 14 , Zn 15 , and Ni 16 were extensively used to synthesize propargylamines. Among these metals, cationic gold species have received special attention because of their effective catalytic activity in A 3 coupling reactions 17,18 .…”

Section: Introductionmentioning

confidence: 99%

Anchorage of Au3+ into Modified Isoreticular Metal–Organic Framework-3 as a Heterogeneous Catalyst for the Synthesis of Propargylamines

Liu

Tai

Zhou

et al. 2017

Sci Rep

View full text Add to dashboard Cite

Postsynthetic modification of metal-organic framework is a general and practical approach to access MOF-based catalysts bearing multiple active sites. The isoreticular metal–organic framework-3 (IRMOF-3) was modified with lactic acid through condensation reaction of the carboxyl group of lactic acid and amino group present in IRMOF-3 frameworks. Au3+ was subsequently anchored onto the metal–organic framework IRMOF-3 using postsynthetic modification. The synthezized IRMOF-3-LA-Au (LA = lactic acid) was characterized by powder X-ray diffraction, N2 adsorption-desorption, infrared spectroscopy, liquid-state nuclear magnetic resonance, thermogravimetric analysis, H2-temperature programmed reduction, transmission electro microscopy, and inductively coupled plasma–optical emission spectrometry. IRMOF-3-LA-Au acted as an efficient heterogeneous catalyst in the synthesis of propargylamines by three-component coupling reaction of aldehyde, alkyne, and amine. Moreover, the catalyst is applicable to various substituted substrates, including aromatic and aliphatic aldehydes, alkyl- and aryl-substituted terminal alkynes, and alicyclic amines. In addition, the catalyst can be easily separated from the mixture and can be reused for four consecutive cycles.

show abstract

“…Among the various metals, the most studied metal for the A 3 ‐coupling reaction was copper . The majority of these catalytic systems are homogeneous, making the recovery and recycling of the catalyst difficult; however, there are some reports on heterogeneous catalysts in the literature, such as Cu 0 ‐nanoparticles (Cu NPs) on montmorillonite, silica‐immobilized CuI, Cu NPs/Mag silica, Cu NPs/TiO 2 , impregnated Cu on magnetite, CuI supported on amberlyst A‐21, Cu NPs stabilized on nitrogen‐doped carbon nanotubes, silica‐gel‐anchored copper chloride, graphene oxide‐supported CuCl 2 , mesoporous copper–aluminum based nanocomposites, Cu 2 O/nano‐CuFe 2 O 4 , lanthanum‐loaded CuO NPs, alumina‐supported Cu NPs, copper ferrite NPs, [Cu(N 2 S 2 )]Cl‐Y, copper modified spherical MCM‐41 NPs, nano copper(I) oxide zinc oxide, Cu–Ni bimetallic, Cu NPs/graphene, Cu NPs/starch micro particles, Cu 2 (BPDC) 2 (BPY), a Cu II Schiff base complex immobilized on graphene oxide and an amino acid ionic‐liquid‐bound copper Schiff base …”

Section: Introductionmentioning

confidence: 99%

CuI Supported on Protonated Trititanate Nanotubes: A Reusable Catalyst for the One‐Pot Synthesis of Propargylamines via A³‐Coupling

Reddy

Shankar

et al. 2017

Asian J Org Chem

View full text Add to dashboard Cite

CuI catalysts supported on protonated trititanate nanotubes (CuI/HTNT) were prepared and used as catalysts for the synthesis of propargylamines via A 3 (aldehyde, amine and acetylene) coupling under solvent-free conditions. The results revealed that the CuI/HTNT with 5wt% CuI had the best catalytic activity.T he protocol provides access to aw ide range of propargylamines in excellent yields (up to 98 %). The prepared catalysts were characterized by TEM, XRD, N 2adsorption desorption, EDS andI CP-MS analysis. The catalyst can be recovered by centrifugation and reused in further catalytic reactions, its activity remaining largely unchanged for five successive runs.[a] B.

show abstract

Amino acid ionic liquid bound copper Schiff base catalyzed highly efficient three component A3-coupling reaction

Cited by 41 publications

References 30 publications

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Anchorage of Au3+ into Modified Isoreticular Metal–Organic Framework-3 as a Heterogeneous Catalyst for the Synthesis of Propargylamines

CuI Supported on Protonated Trititanate Nanotubes: A Reusable Catalyst for the One‐Pot Synthesis of Propargylamines via A³‐Coupling

Contact Info

Product

Resources

About

Amino acid ionic liquid bound copper Schiff base catalyzed highly efficient three component A3-coupling reaction

Cited by 41 publications

References 30 publications

Polymer supported copper(II) amine‐imine complexes in the C‐N and A3 coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A3 coupling reactions

Anchorage of Au3+ into Modified Isoreticular Metal–Organic Framework-3 as a Heterogeneous Catalyst for the Synthesis of Propargylamines

CuI Supported on Protonated Trititanate Nanotubes: A Reusable Catalyst for the One‐Pot Synthesis of Propargylamines via A3‐Coupling

Contact Info

Product

Resources

About

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

CuI Supported on Protonated Trititanate Nanotubes: A Reusable Catalyst for the One‐Pot Synthesis of Propargylamines via A³‐Coupling