Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions

Alleti, Ramesh; Oh, Woon Su; Perambuduru, Meher; Ramana, Chepuri V.; Reddy, V. Prakash

doi:10.1016/j.tetlet.2008.03.108

Cited by 29 publications

(10 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We design a magnetic nanoparticles-based catalytic The aza-Michael addition reaction of acryl amides is significant for preparing kinds of β-amino carbonyl compounds from readily manufactured raw materials in a sustainable and clean method [41][42][43][44][45][46]. Recently, the researches in aza-Michael addition by the imidazolium-based polymer [47], enzymes [48][49][50][51], and room-temperature ionic liquids (RTILs) have given a novelty way to achieve the important β-amino carbonyl derivatives [28]. These methods definitely have excellent potential as powerful tools which can build multiple molecules with different acryl amides, and in the meantime provide new catalytic cascade reaction sequences.…”

Section: Resultsmentioning

confidence: 99%

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Liu

Luo

et al. 2017

Catalysts

View full text Add to dashboard Cite

Abstract:A nanostructure-based catalytic system has the advantages of both homogeneous and heterogeneous catalysis. It is of great significance to develop the sustainable and green process of homogeneous catalytic reaction. We report a novel, efficient and recyclable magnetic Fe 3 O 4 nanoparticles-catalyzed aza-Michael addition reaction of acryl amides, and the magnetic nanoparticles catalysts can be recovered by external magnetic field. Both primary amine and secondary amine can react with various acryl amides providing a good output to target products successfully at room temperature. Further experiments reveal that the magnetic Fe 3 O 4 nanoparticles-based catalyst shows excellent yields, which can be recycled 10 times, and, at the same time, it maintains a high catalytically activity. In this catalytic system, the tedious separation procedures are replaced by external magnetic field, which gives us a different direction for choosing a catalyst in a nanostructure-based catalytic system.

show abstract

Section: Resultsmentioning

confidence: 99%

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Liu

Luo

et al. 2017

Catalysts

View full text Add to dashboard Cite

show abstract

“…Generally, bases with quaternary/tertiary amine are used for aza‐Michael addition reaction and more recently DABCO, which possesses two tertiary nitrogens (catalytic sites), loaded on Fe 3 O 4 ‐magnetic nanoparticles has been reported to meet the objective . The aza‐Michael reaction by using imidazoline based polymer is also reported . Ying and co‐workers studied solvent free aza‐Michael addition reaction .…”

Section: Introductionmentioning

confidence: 99%

Polymer‐Shell‐Encapsulated Magnetite Nanoparticles Bearing Hexamethylenetetramine for Catalysing Aza‐Michael Addition Reactions

et al. 2018

View full text Add to dashboard Cite

Polymer‐encapsulated magnetite nanoparticles bearing Hexamethylenetetramine (Fe3O4@HMTA) have been developed for catalysing the aza‐Michael addition to form β‐amino compounds. The effects of solvent, amount and reuse on catalytic activity of the Fe3O4@HMTA have been studied. The catalytic activity of the Fe3O4@HMTA has not deteriorated during successive recycling. Eight different substrates have been subjected to aza‐Michael additions, and yields of the products in the range of 50–90 % have been observed in the presence of catalyst depending upon the substituent groups in the reactants. The formation of a single chiral adduct by reacting a acrylamide derivative of l‐proline benzyl ester with morpholine seems to suggest that the reaction conditions preclude the racemization of products.

show abstract

“…However, now a considerable improvement in terms of yield and time has been observed in the Michael addition reaction. In this context, a number of reagents have been developed which include silica nanoparticles, basic ionic liquid, tributylphosphine, poly( N ‐vinylimidazole), st‐DNA, tetraethylammonium superoxide, KF/CP, [C 4 dabco]OH ionic liquid, Rasta resin, immobilized lipase on Fe 3 O 4 /ZnO core/shell magnetic nanoparticles, polyvinyl sulfonic acid, silica sulfuric acid, KG‐60‐NEt 2 , KF/NP, NaHSO 4 .SiO 2 , 1 ‐Gd(OTf) 3 , Kf/basic alumina, Zn‐HAP and CSC‐Star‐SO 3 AlCl 2 . Moreover, most of the reactions are referred to mono‐Michael addition reaction, and very few reagents have been reported for the bis‐Michael addition reaction to date .…”

Section: Introductionmentioning

confidence: 99%

Aminopropylated PEG as a novel, eco‐friendly and biodegradable basic catalyst for bis‐Michael addition to α,β‐unsaturated ketones under solvent‐free conditions

Khan

Siddiqui

2014

Applied Organom Chemis

View full text Add to dashboard Cite

A solvent-free and highly efficient protocol has been developed for the synthesis of novel bis-Michael addition products (3a-o) using aminopropylated PEG-6000 (NH 2 -PEG) as a biodegradable and recyclable catalyst in excellent yields under solvent-free conditions. Other remarkable features of this environmentally benign protocol are shorter reaction time, tolerance of a wide range of C-H-activated acids, high yield of products, and simple experimental and work-up procedure as compared to conventional methods. The NH 2 -PEG catalyst is characterized by using FT-IR, powder XRD and scanning electron microscopyenergy dispersion X-ray spectrometric analyses. The catalyst can be recycled several times without significant loss of its catalytic activity.

show abstract

Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions

Cited by 29 publications

References 32 publications

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Polymer‐Shell‐Encapsulated Magnetite Nanoparticles Bearing Hexamethylenetetramine for Catalysing Aza‐Michael Addition Reactions

Aminopropylated PEG as a novel, eco‐friendly and biodegradable basic catalyst for bis‐Michael addition to α,β‐unsaturated ketones under solvent‐free conditions

Contact Info

Product

Resources

About