Alkylation of Aniline with Benzyl Alcohol by Using Ni/O‐Clay: Kinetic Studies

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract This study investigates the alkylation of aniline using benzyl alcohol over a Ni (30)/O‐clay catalyst, focusing on optimizing reaction conditions and understanding kinetics. The catalyst demonstrated 70% conversion with 75% selectivity toward benzylideneaniline (BDA) at 343 K in 6‐hour time. Catalyst characterization was performed BET, NH 3 ‐TPD, XRD, FE‐SEM techniques, revealing mesoporous structure strong medium acidic sites that enhance catalytic activity. Key parameters influencing reaction, including temperature, molar ratio, loading, oxidants, solvents, were systematically investigated. Weisz‐Prater criterion confirmed absence mass transfer resistance, kinetic studies validated Langmuir‐Hinshelwood‐Hougen‐Watson (LHHW) mechanism. activation energy calculated found to be 37 kcal/mol. exhibited excellent reusability, maintaining activity up four cycles. work highlights potential Ni‐organoclay for green, cost‐effective synthesis alkylated derivatives, paving way sustainable efficient industrial processes. results emphasize importance heterogeneous catalysts enhancing minimizing by‐products environmentally friendly chemical transformations.

Language: Английский

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A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(13), P. 3044 - 3049

Published: Jan. 1, 2018

We demonstrate a borrowing hydrogen methodology using the p-benzylpalladium system, which offers an efficient and environmentally friendly dehydrative N-monobenzylation of 2-aminopyridines with benzylic alcohols in absence base.

Language: Английский

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NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines

Tetrahedron, Journal Year: 2019, Volume and Issue: 75(18), P. 2697 - 2705

Published: March 28, 2019

Language: Английский

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α-Alkylation of Nitriles with Alcohols Catalyzed by NNN′ Pincer Ru(II) Complexes Bearing Bipyridyl Imidazoline Ligands

Organometallics, Journal Year: 2019, Volume and Issue: 38(9), P. 2156 - 2166

Published: April 23, 2019

A series of unsymmetrical NNN′ ruthenium(II) complexes supported by a tridentate bipyridyl imidazoline ligand with variable steric hindrance (2a–c; R1 = tBu, iPr, or Bn) and electronic effect (2d–h; R2 H, CH3, OCH3, Br, NO2) were prepared. The molecular structures ligands 1f 1g, Ru complex 2a further determined X-ray single-crystal diffraction. catalytic activity these eight for α-alkylation nitriles alcohols was evaluated, which could be controlled the substituents on moiety. 2h bearing strong electron-withdrawing group (R2 demonstrated highest activity, alkylated achieved in up to 97% yield.

Language: Английский

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Selective N‐Monomethylation of Amines and Nitroarenes using Methanol over an Encapsulated Iridium Nanocatalyst

Asian Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 8(4), P. 487 - 491

Published: March 4, 2019

Abstract A highly selective N‐monomethylation of aniline and nitrobenzene using methanol as methylating reagent was achieved with high efficiency when an encapsulated iridium nanocatalyst. wide range amines nitro compounds reacted well in the established catalytic system moderate to excellent product yields good functional group tolerance. The transfer hydrogenation successive cyclization coupling reaction ortho ‐phenylenediamine afford benzimidazole N ‐methylbenzimidazole also efficiently realized under conditions. Recycling experiments showed that nanocatalyst had a stability without obvious activity loss.

Language: Английский

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Recent Advances in the Protection of Amine Functionality: A Review

ChemistrySelect, Journal Year: 2020, Volume and Issue: 5(23), P. 6861 - 6893

Published: June 17, 2020

Abstract Selective protection of −NH 2 functionality has enormous utility and significance in organic synthesis. Amines are nucleophile basic nature thus vulnerable to react with an extensive range reagents, especially oxidizing, alkylating, carbonyl compounds therefore can require mask these properties the multifunctional molecule during chemical reactions. Protection amine finds important application peptide synthesis, several methodologies have been developed for N‐Protection reaction. Herein, we reviewed recent advances amines (from 2012 till present) hope that this will update current body knowledge aid researchers working area.

Language: Английский

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NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 947 - 958

Published: Dec. 22, 2020

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various alcohols are well tolerated to generate the desired products in 44–99% yields without transition metals external additives.

Language: Английский

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Facile synthesis of quinolines and N-alkylation reactions catalyzed by ruthenium(II) pincer type complexes: Reaction mechanism and evidences for ruthenium hydride intermediate

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 549, P. 113424 - 113424

Published: Aug. 19, 2023

Language: Английский

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Mechanistic studies on the N-alkylation of amines with alcohols catalysed by iridium(i) complexes with functionalised N-heterocyclic carbene ligands

Catalysis Science & Technology, Journal Year: 2018, Volume and Issue: 8(9), P. 2381 - 2393

Published: Jan. 1, 2018

Experimental and theoretical studies give support for an iridium-catalyzed C–N bond formation.

Language: Английский

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N-Heterocyclic Carbene-Supported Nickel-Catalyzed Selective (Un)Symmetrical N-Alkylation of Aromatic Diamines with Alcohols

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1135 - 1146

Published: Jan. 5, 2023

The "borrowing hydrogen" (BH) approach for the N-alkylation of phenylenediamines using alcohols as coupling partners is highly challenging due to selectivity issue generated products. Furthermore, development base-metal systems that can potentially substitute precious metals with competitive activity a major challenge in BH catalysis. We present herein an efficient protocol N,N'-di-alkylation aromatic diamines situ-generated Ni-NHC complex from NiCl2 and ligand L1, which gave access wide range N,N'-di-alkylated orthophenylene (rather than generally observed benzimidazole derivatives), meta- para-phenylene along 2,6-diamino pyridine derivatives good excellent yields. Moreover, catalyst system was also successful derivatization clinically important drug molecule, Dapsone. Notably, could be applied effectively synthesize unsymmetrically substituted via sequential alkylation first report best our knowledge. Diverse control experiments including deuterium incorporation studies suggest proceeds sequence.

Language: Английский

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