Nickel complexes bearing quinoline derived NNS donor ligands as catalytic activators for N‐alkylation of anilines with alcohols DOI

Deepika Tanwar,

Suman Mahala, Deepali Ahluwalia

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 12, 2024

Abstract Herein, we have reported a new series of NNS‐donor ligands coordinated Ni(II) complexes and utilized them as catalytic activator to synthesize N ‐alkylated amines 1,2‐disubstituted benzimidazoles. The reaction thiophenol/4‐chlorothiophenol/4‐methylthiophenol/4‐methoxythiophenol with 2‐bromo‐ ‐quinolin‐8‐yl‐acetamide in presence sodium hydroxide ethanol at 80 °C gave [C 9 H 6 N‐NH−C(O)−CH 2 ‐S−Ar] [Ar=C 5 ( L1 ); C 4 Cl‐4 (L2 Me‐4 (L3 ) ‐OMe‐4 (L4 )], respectively. corresponding ‐ L4 Ni(OAc) methanol for 3 hours resulted octahedral nickel [( ‐H) Ni] C1 ), L2 C2 L3 C3 C4 All compounds been characterized by micro spectroscopic analysis. molecular structure – has also determined single crystal X‐ray diffraction data. utility were evaluated the ‐alkylation aniline benzyl alcohols, benzimidazoles synthesis. obtained results indicate that complex showed better activity both alcohols [catalyst loading: 2.0 mol %; Yield up 92 %], derivatives 94 %)]. mechanistic studies suggested works through hydrogen borrowing from alcohol its subsequent utilization situ reduction imine. experimentally observed reactivity patterns found good agreement HOMO‐LUMO energy gaps DFT analysis complexes.

Язык: Английский

One-step reductive amination of 5-hydroxymethylfurfural to 2,5-bis(aminomethyl)furan over a core–shell structured catalyst DOI
Peng Liu, Xiaolong Li, Hong‐Yu Zhang

и другие.

Journal of Catalysis, Год журнала: 2024, Номер 429, С. 115291 - 115291

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

11
Metal–organic framework-derived CoNx nanoparticles on N-doped carbon for selective N-alkylation of aniline DOI Creative Commons

Ved Vyas,

Priyanka Maurya, Arindam Indra

и другие.

Chemical Science, Год журнала: 2023, Номер 14(43), С. 12339 - 12344

Опубликована: Янв. 1, 2023

The Co–N coordination in CoN x @NC (NCN-doped carbon) was found to be beneficial producing high conversion efficiency and yield for secondary amines the N -alkylation reaction between alcohol aniline.

Язык: Английский

Процитировано

12
Microwave-Assisted Synthesis of E-Aldimines, N-Heterocycles, and H2 by Dehydrogenative Coupling of Benzyl Alcohol and Aniline Derivatives Using CoCl2 as a Catalyst DOI
Adwitiya Pal, Krishna Mohan Das, Arunabha Thakur

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8955 - 8968

Опубликована: Июнь 9, 2023

The acceptorless dehydrogenative coupling (ADC) between alcohols and amines to produce imines has been achieved mostly by employing precious-metal-based complexes or of earth-abundant metal ions with sensitive complicated ligand systems as catalysts under harsh reaction conditions. Methodologies using readily available salts without the requirement ligand, oxidant, any external additives are not explored. We report an unprecedented microwave-assisted CoCl2-catalyzed benzyl alcohol amine for synthesis E-aldimines, N-heterocycles, H2 mild condition, exogenous template, other additives. This environmentally benign methodology exhibits broad substrate scope (43 including 7 new products) fair functional-group tolerance on aniline ring. Detection metal-associated intermediate gas chromatography (GC) HRMS, detection GC, kinetic isotope effect reveal mechanism this be via ADC. Furthermore, experiments Hammett analysis variation in nature substituents over ring insight into different substituents.

Язык: Английский

Процитировано

11
Iron-nickel alloy particles with N-doped carbon “armor” as a highly selective and long-lasting catalyst for the synthesis of N-benzylaniline molecules DOI
Gang Wang, Longchao Sun, Wanyi Liu

и другие.

Nano Research, Год журнала: 2023, Номер 17(4), С. 2308 - 2319

Опубликована: Сен. 8, 2023

Язык: Английский

Процитировано

9
The recyclable non-metal acid-catalyzed ammination of benzyl alcohol DOI
Ming Zhong, Min Li, Guoliang Chen

и другие.

Sustainable Chemistry and Pharmacy, Год журнала: 2025, Номер 44, С. 101957 - 101957

Опубликована: Март 3, 2025

Язык: Английский

Процитировано

0
Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions DOI
Max Roemer, Nicholas Proschogo, Ian J. Luck

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1522 - 1532

Опубликована: Янв. 20, 2023

Selective azidation-amination of long-chain alkanoyl halobenzenes with sodium azide, promoted by copper(I) chloride, is reported. The protocol is, apart from CuCl and NaN3, additive free allows the isolation versatile amine-azides. Alkyl cleavage occurs as a side reaction through an unusual Schmidt-type azide insertion adjacent to carbonyl group, forming alkyl nitriles possibly via radical pathways. Mechanistic studies involving 15N labeling experiments test substrates indicate that 1-azido-4-alkanoyl benzenes. amination applicable for electron-withdrawing groups proceeds under mild conditions. mechanism amine formation involves nitrenes. Intermediates were trapped carrying out in presence 2,2,6,6-(tetramethylpiperidin-1-yl)oxyl stable characterized high-resolution mass spectrometry. intermediates are consistent earlier mechanistic proposals.

Язык: Английский

Процитировано

4
Pore size-tunable core-shell structured Ni-Ru Nanoparticles catalyst for the reductive amination of isosorbide diketone DOI
Peng Liu, Hong‐Yu Zhang, Yaping Han

и другие.

Chemical Engineering Journal, Год журнала: 2023, Номер 476, С. 146820 - 146820

Опубликована: Окт. 20, 2023

Язык: Английский

Процитировано

4
Development of a Graphene Oxide-Supported N-Heterocyclic Carbene Copper(I) Complex as a Heterogeneous Catalyst for the Selective N-Monoalkylation of Amines DOI Open Access
Shelly Kujur, Shruti Verma, Devendra D. Pathak

и другие.

Catalysts, Год журнала: 2022, Номер 12(11), С. 1458 - 1458

Опубликована: Ноя. 17, 2022

A new N-heterocyclic carbene (NHC) copper(I) complex supported on graphene oxide (GO-NHC-Cu) was synthesised and thoroughly characterised by various instrumental techniques such as FT-IR, FT-Raman, PXRD, XPS, FESEM, EDX, HRTEM, TGA ICP-OES. The catalytic activity of the explored in N-alkylation anilines with alcohols under solvent-free aerobic conditions to afford monoalkylated products good excellent yields (20 products, 83–96%). All were isolated 1H 13C{1H} NMR spectroscopy. catalyst recuperated from reaction mixture simple filtration reused for up five successive cycles insignificant loss activity. control experiments showed that proceeded conditions. green chemistry metrics found be fairly close ideal values: carbon efficiency (95.9%), E-factor (0.15), atom economy (92.14%), process mass intensity (1.15) (86.80%). air stability, selectivity, recyclability catalyst, high are some salient features reported methodology.

Язык: Английский

Процитировано

6
A facile, one-pot reductive alkylation of aromatic and heteroaromatic amines in aqueous micellar media: a chemoenzymatic approach DOI
Krithika Ganesh, Ganesh Sambasivam, S. Karthikeyan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(20), С. 4264 - 4268

Опубликована: Янв. 1, 2023

A facile, green, selective and practical method for the catalytic N-alkylation of amines using molecular hydrogen as reductant was developed. This procedure involves a lipase-mediated one-pot chemoenzymatic cascade wherein an amine undergoes reductive amination with aldehyde generated in situ. The imine formed thereby is reduced to give corresponding amine. process represents convenient, environmentally benign scalable synthesis N-alkyl amines. We report first time alkylation aqueous micellar media E-factor 0.68.

Язык: Английский

Процитировано

1
Nickel complexes bearing quinoline derived NNS donor ligands as catalytic activators for N‐alkylation of anilines with alcohols DOI

Deepika Tanwar,

Suman Mahala, Deepali Ahluwalia

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 12, 2024

Abstract Herein, we have reported a new series of NNS‐donor ligands coordinated Ni(II) complexes and utilized them as catalytic activator to synthesize N ‐alkylated amines 1,2‐disubstituted benzimidazoles. The reaction thiophenol/4‐chlorothiophenol/4‐methylthiophenol/4‐methoxythiophenol with 2‐bromo‐ ‐quinolin‐8‐yl‐acetamide in presence sodium hydroxide ethanol at 80 °C gave [C 9 H 6 N‐NH−C(O)−CH 2 ‐S−Ar] [Ar=C 5 ( L1 ); C 4 Cl‐4 (L2 Me‐4 (L3 ) ‐OMe‐4 (L4 )], respectively. corresponding ‐ L4 Ni(OAc) methanol for 3 hours resulted octahedral nickel [( ‐H) Ni] C1 ), L2 C2 L3 C3 C4 All compounds been characterized by micro spectroscopic analysis. molecular structure – has also determined single crystal X‐ray diffraction data. utility were evaluated the ‐alkylation aniline benzyl alcohols, benzimidazoles synthesis. obtained results indicate that complex showed better activity both alcohols [catalyst loading: 2.0 mol %; Yield up 92 %], derivatives 94 %)]. mechanistic studies suggested works through hydrogen borrowing from alcohol its subsequent utilization situ reduction imine. experimentally observed reactivity patterns found good agreement HOMO‐LUMO energy gaps DFT analysis complexes.

Язык: Английский

Процитировано

0