Catalytic activity of copper(II) benzenetricarboxylate (HKUST-1) in reactions of aromatic aldehydes condensation with nitromethane: Kinetic and diffusion study

Sotnik, S. A.; Gavrilenko, Konstantin S.; Lytvynenko, Anton; Kolotilov, Sergey V.

doi:10.1016/j.ica.2014.11.018

Cited by 19 publications

(10 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Upon using NiBDP@Cu as the catalyst, 81 % conversion of benzaldehyde and 94 % selectivity to 1 were obtained after 48 h, which supported the use of Cu as a catalyst for the nitroaldol reaction . NiBDP@Cu clearly outperformed the other copper MOFs such as CuBTC, which only converted 2 % of the aldehyde after 60 h of reaction with an excess amount of nitromethane at 100 °C . A hot‐filtration test confirmed the heterogeneous nature of the catalytic process, as the reaction stopped completely after the removal of NiBDP@Cu from the liquid reaction mixture (Figure S20).…”

Section: Methodsmentioning

confidence: 99%

Selective One‐Pot Two‐Step C−C Bond Formation using Metal–Organic Frameworks with Mild Basicity as Heterogeneous Catalysts

et al. 2017

View full text Add to dashboard Cite

Copper‐ion‐exchanged nickel pyrazolate frameworks behave as selective heterogeneous catalysts for the one‐pot, two‐step (Henry reaction/Michael type addition) synthesis of neuroactive pharmaceutical intermediates starting from nitromethane and benzaldehyde. Tuning the basicity of multifunctional metal–organic framework catalysts through ion exchange with copper(II) cations allows the tandem C−C bond‐forming process to be selectively directed towards the desired pharmaceutical intermediate.

show abstract

Section: Methodsmentioning

confidence: 99%

Selective One‐Pot Two‐Step C−C Bond Formation using Metal–Organic Frameworks with Mild Basicity as Heterogeneous Catalysts

et al. 2017

View full text Add to dashboard Cite

show abstract

“…In another precedent, the molecular-sieving effect of HKUST-1 was reported in the Henry reaction between aromatic aldehydes with nitromethane. The experimental results have shown that the reaction of salicylaldehyde with nitromethane, in the presence of HKUST-1, to obtain trans-nitrovinylphenol, is much faster, while no reaction occurred with 9-anthracenecarbaldehyde [ 37 ]. The difference in catalytic performance of HKUST-1 with salicylaldehyde and 9-anthracenecarbaldehyde is due to the sieving effect of this catalyst, which clearly discriminates by size.…”

Section: Metal Nodes As Active Sitesmentioning

confidence: 99%

Metal-Organic Frameworks as Versatile Heterogeneous Solid Catalysts for Henry Reactions

2021

View full text Add to dashboard Cite

Metal–organic frameworks (MOFs) have become one of the versatile solid materials used for a wide range of applications, such as gas storage, gas separation, proton conductivity, sensors and catalysis. Among these fields, one of the more well-studied areas is the use of MOFs as heterogeneous catalysts for a broad range of organic reactions. In the present review, the employment of MOFs as solid catalysts for the Henry reaction is discussed, and the available literature data from the last decade are grouped. The review is organized with a brief introduction of the importance of Henry reactions and structural properties of MOFs that are suitable for catalysis. The second part of the review discusses the use of MOFs as solid catalysts for the Henry reaction involving metal nodes as active sites, while the third section provides data utilizing basic sites (primary amine, secondary amine, amides and urea-donating sites). While commenting on the catalytic results in these two sections, the advantage of MOFs over other solid catalysts is compared in terms of activity by providing turnover number (TON) values and the structural stability of MOFs during the course of the reaction. The final section provides our views on further directions in this field.

show abstract

“…However, the desirable catalytic features of MOFs have rarely been applied to annulations, especially for cascade reactions. HKUST‐1, as a crystalline organic−inorganic hybrids, has been employed as a promising catalyst for the condensation of aldehydes with nitromethane, and deacetalization–Knoevenagel reaction . We report herein an efficient HKUST‐1‐catalyzed sequential amination/annulation/ aromatization reaction of carbonyl compounds and N ‐propargylamine (Eq.…”

Section: Introductionmentioning

confidence: 99%

HKUST‐1‐Catalyzed Formation of C–C and C‐N Bonds: Rapid Assembly of Substituted Pyridines from Propargylamine and Carbonyl Compounds

Meng

Kang

et al. 2018

ChemistrySelect

View full text Add to dashboard Cite

An efficient synthesis of 2,3‐fused pyridines through a HKUST‐1 (copper(II) 1,3,5‐benzenetricarboxylate) catalyzed sequential amination/annulation/aromatization reaction of carbonyl compounds and N‐propargylamine is presented herein. The reaction is not restricted to reactive ketones, wherein the five‐, six‐membered cyclic ketones and benzyl, aryl ketones show good reactivity with N‐propargylenamine, delivering pyridines in moderate to good yields. Under reaction conditions devoid of high temperature and expensive catalyst, this method exhibits broad tolerance of functional groups, including CN, alkyl, benzyl and methoxy moieties as well as unprotected phenolic hydroxy group. Additionally, the role of organic link for HKUST‐1 has been considered as a key parameter for this transformation.

show abstract

Catalytic activity of copper(II) benzenetricarboxylate (HKUST-1) in reactions of aromatic aldehydes condensation with nitromethane: Kinetic and diffusion study

Cited by 19 publications

References 42 publications

Selective One‐Pot Two‐Step C−C Bond Formation using Metal–Organic Frameworks with Mild Basicity as Heterogeneous Catalysts

Selective One‐Pot Two‐Step C−C Bond Formation using Metal–Organic Frameworks with Mild Basicity as Heterogeneous Catalysts

Metal-Organic Frameworks as Versatile Heterogeneous Solid Catalysts for Henry Reactions

HKUST‐1‐Catalyzed Formation of C–C and C‐N Bonds: Rapid Assembly of Substituted Pyridines from Propargylamine and Carbonyl Compounds

Contact Info

Product

Resources

About