Diastereoselective Mannich reaction with prolinated MWCNTs as a heterogeneous organo-nanocatalyst

Khoshnevis, Mahsa

doi:10.1007/s12039-020-1740-4

Cited by 7 publications

(9 citation statements)

References 29 publications

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“…At the first step, synthesis of hydroxylated MWCNTs (MWCNT‐OH) was performed according to method discussed in previously reported article. [ 42 ]…”

Section: Methodsmentioning

confidence: 99%

“…At the first step, synthesis of hydroxylated MWCNTs (MWCNT-OH) was performed according to method discussed in previously reported article. [42] MWCNT-OH (0.5 g) and epibromohydrin (2.5 mL) in the presence of absolute EtOH (50 mL) were sonicated for 20 min at room temperature; then, the mixture was stirred at 60 C, and after 24 h, the produced EP-MWCNTs were centrifuged and washed truly with absolute EtOH and dried in the oven at 50 C.…”

Section: Functionalization Of Mwcnt-oh With Epibromohydrin (Ep-mwcnt)mentioning

confidence: 99%

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Anchoring Cu nanoparticles on functionalized multi‐walled carbon nanotube for regioselective synthesis of 1,2,3‐triazoles via click reaction

Khoshnevis

2021

Applied Organom Chemis

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Unique properties of 1,2,3-triazoles on the one hand and necessity of usage of an efficient catalyst with fidelity in principles of green chemistry on the other hand impelled us to design and synthesis of a novel heterogeneous nanocatalyst (Cu@Arg-MWCNTs) with simple synthesis, immense power, high regioselectivity, and easy separation and recyclability. The Cu@Arg-MWCNT structure is characterized by different analyses and used for the synthesis of various triazoles. Its high catalytic activity is confirmed by high yields and short reaction times under mild conditions in click reaction.

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“…At the first step, synthesis of hydroxylated MWCNTs (MWCNT‐OH) was performed according to method discussed in previously reported article. [ 42 ]…”

Section: Methodsmentioning

confidence: 99%

Section: Functionalization Of Mwcnt-oh With Epibromohydrin (Ep-mwcnt)mentioning

confidence: 99%

Anchoring Cu nanoparticles on functionalized multi‐walled carbon nanotube for regioselective synthesis of 1,2,3‐triazoles via click reaction

Khoshnevis

2021

Applied Organom Chemis

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“…Based on the reported related literature, a plausible reaction mechanism of the Mannich reaction is proposed, as shown in Scheme 3 [75,79]. First, activated aryl aldehyde 6 via coordination with [BCMIM][Cl] 4, reacts with arylamine 7 to give intermediate imine by condensation.…”

Section: Plausible Reaction Mechanismmentioning

confidence: 99%

[BCMIM][Cl] ionic liquid catalyzed diastereoselective synthesis of β‐amino ketones via facile, one‐pot, multicomponent Mannich reaction under solvent‐free condition

Mohurle,

Pasuparthy

et al. 2023

Journal of Heterocyclic Chem

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In this work, by utilizing 6 mol% of 1,3‐bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] ionic liquid as a catalyst, a highly effective diastereoselective one‐pot multicomponent Mannich reaction has been established. The three components, namely, cyclohexanone, substituted aromatic aldehydes, and substituted aromatic amines, underwent the Mannich reaction efficiently under the solvent‐free condition at room temperature in the presence of 6 mol% [BCMIM][Cl] catalyst to afford the desired β‐amino ketones. Excellent diastereoselectivity, rapid reaction times, high yields, and no purification by column chromatography are the key characteristics of this process. All synthesized derivatives were thoroughly characterized and confirmed using 1H NMR, 13C NMR, and Fourier‐transform infrared spectral methods. Moreover, the catalytic activity of the [BCMIM][Cl] ionic liquid catalyst was maintained after being reprocessed and used three times.

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“…The content of L-proline in the obtained catalyst is only about 10 wt.% (i.e., 1.27 wt.% of N) [27]. Tagmatarchis [28] and Eshghi [29] reported the covalent functionalization of the MWCNTs with the proline derivatives, giving the maximum loading of 15 wt.% and 7 wt.%, respectively. When the catalysts are applied in Aldol reaction or Mannich reaction, although the yield of the product is up to 95%, the catalytic efficiency decreases dramatically after only 3 or 5 rounds of recycling.…”

Section: Of 10mentioning

confidence: 99%

On the Exceptionally High Loading of L-Proline on Multi-Wall Carbon Nanotubes

Liang

Huang

et al. 2020

Catalysts

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L-proline is directly loaded on the multi-wall carbon nanotubes (MWCNTs) with exceptionally high loading content of 67 wt.%. The obtained L-proline/MWCNTs catalyst is on par with the catalytic activity of free L-proline, even after 7 rounds of recycling and reusing. The excellent activity of L-proline/MWCNTs in typical Aldol reaction, Mannich reaction, Michael reaction, α-oxyamination reaction, and Knoevenagel condensation shows a broad applicability of the composite catalyst in different reactions and solvent systems. We believe that the unusual loading mode may open a window for designing heterogenized organo-catalysts.

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Diastereoselective Mannich reaction with prolinated MWCNTs as a heterogeneous organo-nanocatalyst

Cited by 7 publications

References 29 publications

Anchoring Cu nanoparticles on functionalized multi‐walled carbon nanotube for regioselective synthesis of 1,2,3‐triazoles via click reaction

Anchoring Cu nanoparticles on functionalized multi‐walled carbon nanotube for regioselective synthesis of 1,2,3‐triazoles via click reaction

[BCMIM][Cl] ionic liquid catalyzed diastereoselective synthesis of β‐amino ketones via facile, one‐pot, multicomponent Mannich reaction under solvent‐free condition

On the Exceptionally High Loading of L-Proline on Multi-Wall Carbon Nanotubes

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