Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy DOI
Pennamuthiriyan Anandaraj, Rengan Ramesh, J.G. Małecki

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

A facile, cost-effective, and sustainable synthesis of substituted triazines from primary alcohols by newly synthesized nickel pincer-type complexes (1–3) has been described. Herein, we report the a set three well-defined Ni(II) O^N^O complexes, structurally characterized analytical, spectral, X-ray diffraction techniques. Further, are explored as efficient catalysts (4 mol %) for construction 2,4,6-substituted 1,3,5-triazines readily available via an acceptorless dehydrogenative coupling (ADC) strategy. wide range triazine derivatives (33 examples) benzamidine/guanidine hydrochloride with maximum isolated yield 92% under mild conditions, eco-friendly H2O H2 gas only byproducts. plausible mechanism proposed based on sequence control experiments. Interestingly, short antiulcer drug irsogladine large-scale 2,4-diphenyl-6-(p-tolyl)-1,3,5-triazine highlight convenience current methodology.

Language: Английский

Inducing Cu Charge Redistribution by Modulating Proximity with Zr(OH)4 for Selective Synthesis of Imines and Secondary Amines with Stoichiometric Benzyl Alcohol and Nitrobenzene DOI
Jie Song,

Chunxia Che,

Yiwei Dai

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1170 - 1181

Published: Jan. 6, 2025

The one-pot synthesis of amines from benzyl alcohol (BA) and nitrobenzene (NB) represents a step-economic method. However, reported works typically require more than 3 equiv BA to complete the transfer hydrogenation NB, few studies can achieve selective imines secondary amines. In our previous work, Zr(OH)4 demonstrated both dehydrogenation capabilities. Building on this, another component Cu was introduced enhance its catalytic performance for catalyzing coupling reaction between stoichiometric NB under H2 atmosphere. physical hybrid catalyst + selectively produced imines, while supported Cu/Zr(OH)4 yielded Characterization mechanism experiments revealed that modulating proximity leads (1) different adsorption abilities N-benzylideneaniline (NBA) (2) interactions in close contact, which stabilized electronic structure forming Cu+/Cu0 ion pairs with strong activation ability. This work presents design strategy offers an approach preparation N-benzylaniline.

Language: Английский

Citations

1
Single-atom Co sites with upshifted d-band center efficiently boost transfer hydrogenation for selective imines synthesis DOI
Ting Zhang,

Wantong Zhao,

Shiyan Li

et al.

Chemical Engineering Journal, Journal Year: 2024, Volume and Issue: 484, P. 149614 - 149614

Published: Feb. 13, 2024

Language: Английский

Citations

8
Low‐Temperature N‐Alkylation of Amines with Alcohols in Protic Solvents Catalyzed by Iridium Complexes Bearing N‐Heterocyclic Carbenes DOI

Shohichi Furukawa,

Namino Morishima,

Ken‐ichi Fujita

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(6)

Published: Jan. 1, 2024

Abstract Amines are important compounds found in natural products, pharmaceuticals, and fine chemicals. Therefore, the development of elegant, environmentally friendly, simple synthetic methods is desirable. Recently, borrowing‐hydrogen (BH) strategy has received considerable attention for C−N bond formations because its high atomic efficiency absence toxic waste generation. Researchers have recently reported that use N‐heterocyclic carbene (NHC) ligands with strong electron‐donating properties protic solvents can increase catalytic activity BH strategy. herein, we focused on versatility methods, such as a system allows synthesis, operates at low reaction temperatures, involves effective solvent simultaneously. The catalyzed N‐alkylation alcohols amines under mild conditions was investigated using NHC complexes developed by our group. We achieved synthesis various alkylamines conditions, 40–60 °C, iridium comprising structures 2,2,2‐trifluoroethanol 1,1,1,3,3,3‐hexafluoroisopropanol.

Language: Английский

Citations

5
Ruthenium Complexes with NNN-Pincer Ligands for N-Methylation of Amines Using Methanol DOI

Mengxuan Bai,

Shengxin Zhang,

Zhengguo Lin

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(25), P. 11821 - 11831

Published: June 7, 2024

A series of ruthenium complexes (Ru1–Ru4) bearing new NNN-pincer ligands were synthesized in 58–78% yields. All the are air and moisture stable characterized by IR, NMR, high-resolution mass spectra (HRMS). In addition, structures Ru1–Ru3 confirmed X-ray crystallographic analysis. These Ru(II) exhibited high catalytic efficiency broad functional group tolerance N-methylation reaction amines using CH3OH as both C1 source solvent. Experimental results indicated that electronic effect substituents on considerably affects reactivity which Ru3 an electron-donating OMe showed highest activity. Deuterium labeling control experiments suggested dehydrogenation methanol to generate hydride species was rate-determining step reaction. Furthermore, this protocol also provided a ready approach versatile trideuterated N-methylamines under mild conditions CD3OD deuterated methylating agent.

Language: Английский

Citations

5
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

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(43), P. 12339 - 12344

Published: Jan. 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.

Language: Английский

Citations

12
Molybdenum‐Catalyzed Asymmetric Amination of α‐Hydroxy Esters: Synthesis of α‐Amino Acids DOI Creative Commons
Shahida Perveen, Talat S. Rahman, Tariq Ali

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Abstract Unnatural α‐amino acids are found in a wide variety of bioactive compounds ranging from proteins to pharmaceutical agents materials science. As result, the investigation efficient and simple methods for their synthesis is major purpose reaction development. In this study, it that catalyst based on molybdenum, an earth‐abundant transition metal, can facilitate amination readily accessible α‐hydroxy esters afford N ‐protected unnatural acid high yield. This process also enables enantioselective amination, which proceeds through cooperative catalysis chiral molybdenum complex with phosphoric (CPA), complements earlier procedures catalytic important class compounds. The obtained protected ester products directly useful or further utilized commercially available drugs analogs.

Language: Английский

Citations

0
Ligational behavior of a new bis (bidentate NO) donor hydrazone towards Co (II), Ni (II), and Cu (II) ions: Preparation, spectral, thermal, biological, docking, and theoretical studies DOI Open Access
Fatma Samy, Magdy Shebl

Applied Organometallic Chemistry, Journal Year: 2022, Volume and Issue: 36(12)

Published: Sept. 21, 2022

Reaction of 4,6‐bis(1‐hydrazonoethyl)benzene‐1,3‐diol with 3‐nitrobenzaldehyde gave the new bis (bidentate) hydrazone ligand; 4,6‐bis(3‐nitrobenzalen‐1‐yl)methylene)hydrazono)ethyl)benzene‐1,3‐diol (H 2 L; H BisBD). Binuclear Co (II), Ni and Cu (II) complexes general formula ([M BisBD(H O) x (EtOH) y ].nH O; M = Co, or Cu, 4 6, 0; n 1 0) have been successfully prepared. The structures BisBD its characterized by means analytical, spectroscopic (infrared, proton nuclear magnetic resonance, mass, UV–Vis, electron spin resonance), molar conductivity, susceptibility measurements thermal gravimetric analysis. Octahedral geometrical were proposed for all in which ligand behaves as a (monoanionic bidentate) via azomethine nitrogen phenolic oxygen donor atoms. scanning microscopy refers that copper complex is nano scale. showed antitumor activity against Hepatocellular carcinoma. Complexation process improved activity, promising agree docking data. Theoretical studies prepared compounds calculated using Hyperchem program at PM3 .

Language: Английский

Citations

17
Temperature-dependent switchable synthesis of imines and amines via coupling of alcohols and amines using pyrrolyl-imine ruthenium catalysts DOI
Qing Li, Yu Hou,

Mengxuan Bai

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 115895 - 115895

Published: Dec. 1, 2024

Language: Английский

Citations

3
A highly active and chemoselective homobimetallic ruthenium catalyst for one-pot reductive amination in water DOI
Gopal Deshmukh, Thakur Rochak Kumar Rana,

Nikita Yadav

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(3), P. 1610 - 1626

Published: Dec. 13, 2023

A bimetallic Ru( ii ) complex efficiently catalyzes reductive amination of diverse substrates in water with the highest reported TONs and TOFs. Experimental DFT calculations point to a cooperative effect for increased efficiency at low catalyst loading (0.05 mol%).

Language: Английский

Citations

7
Half-Sandwich Iridium Complexes: A Recyclable and Stable Catalyst for Dehydrogenation of Alcohols to Carboxylic Acids DOI
Song Gao,

C.-L. Cao,

Zhenjiang Liu

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(29), P. 13311 - 13320

Published: July 8, 2024

A series of acylhydrazone-based

Language: Английский

Citations

2