Tris-(2-aminoethyl) amine as a novel and efficient tripod ligand for a copper(I)-catalyzed C–O coupling reaction

Jogdand, Nivrutti R.; Shingate, Bapurao B.; Shingare, Murlidhar S.

doi:10.1016/j.tetlet.2009.03.028

Cited by 43 publications

(12 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar results were reported by Chen et al for NB conversion when using 5 mol % of (Cu(OAc) 2 ·H 2 O) as a catalyst and similar reaction conditions [12]. However, it must be pointed out that Cu content for reaching a complete conversion of NB as shown before is significantly lower compared to conventional Ullman reactions, where an average value of 10 mol % Cu-catalyst concentration is needed [27,28]. …”

Section: Resultssupporting

confidence: 82%

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

et al. 2017

View full text Add to dashboard Cite

The activity and recyclability of Cu-MOF-74 as a catalyst was studied for the ligand-free C–O cross-coupling reaction of 4-nitrobenzaldehyde (NB) with phenol (Ph) to form 4-formyldiphenyl ether (FDE). Cu-MOF-74 is characterized by having unsaturated copper sites in a highly porous metal-organic framework. The influence of solvent, reaction temperature, NB/Ph ratio, catalyst concentration, and basic agent (type and concentration) were evaluated. High conversions were achieved at 120 °C, 5 mol % of catalyst, NB/Ph ratio of 1:2, DMF as solvent, and 1 equivalent of K2CO3 base. The activity of Cu-MOF-74 material was higher than other ligand-free copper catalytic systems tested in this study. This catalyst was easily separated and reused in five successive runs, achieving a remarkable performance without significant porous framework degradation. The leaching of copper species in the reaction medium was negligible. The O-arylation between NB and Ph took place only in the presence of Cu-MOF-74 material, being negligible without the solid catalyst. The catalytic advantages of using nanostructured Cu-MOF-74 catalyst were also proven.

show abstract

Section: Resultssupporting

confidence: 82%

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

et al. 2017

View full text Add to dashboard Cite

show abstract

“…The XRD pattern of the Fe 3 O 4 @PVA/CuCl catalyst is depicted in Figure 7. The existence of six peaks at 2θ of 30.5 , 35 [28] 2 C 6 H 5 Br Morpholine 95 [28] 3 C 6 H 5 Cl Morpholine 60 [28] 4 p-NCC 6 H 4 I Morpholine 95 [27] 5 p-NCC 6 H 4 Br Morpholine 92 [27] 6 p-NCC 6 H 4 Cl Morpholine 55 [27] 7 p-CH 3 C 6 H 4 I Morpholine 96 [28] 8 p-CH 3 C 6 H 4 Br Morpholine 90 [28] 9 p-CH 3 OC 6 H 4 I Morpholine 95 [32] 10 p-CH 3 OC 6 H 4 Br Morpholine 90 [32] 11 C 6 H 5 I Piperidine 95 [29] 12 C 6 H 5 Br Piperidine 92 [29] 13 C 6 H 5 Cl Piperidine 55 [29] 14 C 6 H 5 I Indole 92 [27] 15 C 6 H 5 Br Indole 90 [27] 16 C 6 H 5 Cl Indole 60 [27] 17 C 6 H 5 I Imidazole 85 [33] 18 C 6 H 5 Br Imidazole 80 [33] Furthermore, CuCl existence in the Fe 3 O 4 @PVA/CuCl nanostructure was reconfirmed by X-ray photoelectron spectroscopy analysis by studying binding energy range between 930 and 955 eV (Figure 8). The analysis resolved Cu 2p spectrum into two spin-orbit pairs with 932.2 and 952.1 eV binding energies, respectively.…”

Section: Resultsmentioning

confidence: 99%

Cu(I)‐anchored polyvinyl alcohol coated‐magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann‐type C–N coupling reactions

Hemmati

Kamangar

Yousefi

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

In this paper, the preparation of a novel magnetic nanocatalyst (Fe3O4@PVA/CuCl) is described, which involves coating of polyvinyl alcohol (PVA) onto the surface of Fe3O4 nanoparticles and its subsequent coordination with CuCl catalyst. The nanocatalyst was characterized by various analytical methods, including Fourier‐transform infrared, X‐ray diffraction, inductively coupled plasma spectroscopy, field emission scanning electron microscopy, energy‐dispersive X‐ray spectroscopy (EDX), transmission electron microscopy, vibrating‐sample magnetometry, and EDX elemental mapping. Moreover, the nanocatalyst was efficiently used in the N‐arylation of amines via the formation of a carbon–nitrogen bond between the aryl halides and amines by Ullmann‐type coupling reactions. The catalyst was sufficiently stable and can be reused for at least seven times in a model Ullmann reaction without remarkable alteration in its catalytic behavior. Heterogeneity of the catalyst was investigated by a hot filtration test.

show abstract

“…In comparison with reported results (72–95 % yield; Table , entries 13, 15, 16, and 18), the catalytic performance of LaAlPO‐5‐M (>99 % yield; Table , entries 4, 14, 17, and 19) is superior. The excellent catalytic performance of LaAlPO‐5‐M for the Ullmann coupling reaction is attributed to the high and uniform dispersion of La species because of the large surface area and the abundant mesopores, which facilitate the diffusion of the reactant and product molecules.…”

Section: Resultsmentioning

confidence: 99%

“…> 99 (87) -15 [49] Cu II /silica KF 130/16 88 1.1 16 [50] CuI/ligand [ www.chemcatchem.org KOH, and NaOtBu resulted in lower yields (49-71%;T able 2, entries 9-11).…”

Section: Resultsmentioning

confidence: 99%

Ullmann Coupling Reaction of Nitro‐Substituted Aryl Halides with Phenols under Mild Conditions: Micro‐/Mesoporous Hierarchical LaAlPO‐5 Zeolite Catalyst

Wang

et al. 2016

ChemCatChem

View full text Add to dashboard Cite

Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro‐substituted aryl halides were catalyzed by rare‐earth‐doped mesoporous AlPO‐5 zeolites in the absence of ligands. The AlPO‐5‐MAlPO‐5‐M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare‐earth elements were highly dispersed in the AlPO‐5‐MAlPO‐5‐M samples. The LaAlPO‐5‐MAlPO‐5‐M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro‐substituted aryl halides. Mesoporous LaAlPO‐5 has an excellent stability and recyclability in the Ullmann coupling of p‐X‐nitrobenzene (X=Cl, Br, and I) with 2‐naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.

show abstract

Tris-(2-aminoethyl) amine as a novel and efficient tripod ligand for a copper(I)-catalyzed C–O coupling reaction

Cited by 43 publications

References 28 publications

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

Cu(I)‐anchored polyvinyl alcohol coated‐magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann‐type C–N coupling reactions

Ullmann Coupling Reaction of Nitro‐Substituted Aryl Halides with Phenols under Mild Conditions: Micro‐/Mesoporous Hierarchical LaAlPO‐5 Zeolite Catalyst

Contact Info

Product

Resources

About