Dehydrogenation of N‐Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents DOI

Natalia Llopis,

Patricia Gisbert,

Alejandro Baeza

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(6), P. 1205 - 1210

Published: Feb. 11, 2022

Abstract The oxidative dehydrogenation of N ‐heterocyclic compounds by using H 2 O as oxidant in combination with polar solvents such 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) and is described. Among these two solvents, the best yields for heteroaromatic were generally achieved HFIP. However, it remarkable, that use a non toxic solvent gave good yields. Furthermore, procedure was implemented larger‐scale HFIP distilled from reaction mixture reused (up to 5 cycles) without significant detriment outcome. magnified image

Language: Английский

Oxygen-vacancy-boosted visible light driven photocatalytic oxidative dehydrogenation of saturated N-heterocycles over Nb2O5 nanorods DOI

Yinpan Zhang,

Tao Song, Xin Zhou

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2022, Volume and Issue: 316, P. 121622 - 121622

Published: June 11, 2022

Language: Английский

Citations

44

TBAI‐Promoted Electrochemical Cyclization: Synthesis of Quinazolines Using Cascade C—N Bond Generation DOI Open Access
Kamal Kant, Priyadarshini Naik,

Yaqoob A. Teli

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract An electrochemical cyclization strategy is employed herewith for the eco‐friendly and cost‐effective synthesis of 2‐substituted quinazolines by using 2‐aminobenzylamines aldehydes or alcohols as starting substrates. The reactions were conducted under two distinct reaction temperatures: 25 °C 60 alcohols. Tetra‐ n ‐butylammonium iodide (TBAI) participates in dual roles such as, an electrolyte a mild reagent to facilitate formation at constant current 30 mA graphite electrode anode platinum cathode dimethyl sulfoxide (DMSO) solvent. Under devised process, accomplished with broad substrate scope excellent yields (up 90%), which reduces toxic side products. plausible mechanistic pathways have been formulated, are supported control experiments cyclic voltammetry studies. findings demonstrate that conditions, iodonium ions generated, play crucial role enhancing efficacy described method.

Language: Английский

Citations

2

Superstructure‐Induced Hierarchical Assemblies for Nanoconfined Photocatalysis DOI Open Access
Menghao Li, Zhiqiang Yang, Hui Hui

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(47)

Published: Oct. 6, 2023

Abstract Most attempts to synthesize supramolecular nanosystems are limited a single mechanism, often resulting in the formation of nanomaterials that lack diversity properties. Herein, hierarchical assemblies with appropriate variety fabricated bulk via superstructure‐induced organic–inorganic hybrid strategy. The dynamic balance between substructures and superstructures is managed using covalent organic frameworks (COFs) metal–organic (MOFs) as dual building blocks regulate performances assemblies. Significantly, from controlled cascade COFs MOFs create highly active photocatalytic systems through multiple topologies. Our designed tandem photocatalysis can precisely efficiently conversion rates bioactive molecules (benzo[d]imidazoles) competing redox pathways. Furthermore, benzo[d]imidazoles catalyzed by such be isolated yields ranging 70 % 93 within tens minutes. multilayered structural states demonstrate importance facilitating propagation expanding repertoire hybrids.

Language: Английский

Citations

18

A photoactivatable theranostic probe for simultaneous oxidative stress-triggered multi-color cellular imaging and photodynamic therapy DOI
Xiaohong Chen, Zicong Zhang,

Wenshuai Luo

et al.

Biomaterials, Journal Year: 2022, Volume and Issue: 287, P. 121680 - 121680

Published: July 14, 2022

Language: Английский

Citations

22

Visible-Light-Driven Oxidation of Amines to Imines in Air Catalyzed by Polyoxometalate–Tris(bipyridine)ruthenium Hybrid Compounds DOI
Haiyan An, Huiyun Luo, Tieqi Xu

et al.

Inorganic Chemistry, Journal Year: 2022, Volume and Issue: 61(27), P. 10442 - 10453

Published: June 25, 2022

The development of visible-light photocatalysts for the selective oxidative coupling amines to imines is an area great interest. Herein, four hybrid compounds based on polyoxometalate anions and tris(bipyridine)ruthenium cations, Ru(bpy)3[M6O19] (M = Mo, W) 1-2, [Ru(bpy)3]2[Mo8O26] 3, [Ru(bpy)3]2[W10O32] 4, are prepared characterized by X-ray diffraction (single-crystal powder), elemental analysis, energy-dispersive spectroscopy (EDS) infrared (IR) spectroscopy, solid diffuse reflective spectroscopy. Single-crystal structural analysis indicates that cations interact with each other through extensive hydrogen bonds in these compounds. These species strong visible-light-harvesting abilities suitable photocatalytic energy potentials show excellent activity selectivity oxidation at room temperature air as oxidant. Among them, compound 1 [Mo6O19]2- anion has highest catalytic activity, which can swiftly convert >99.0% benzylamine into N-benzylidenebenzylamine a 98.0% 25 min illumination 10 W 445 nm light-emitting diode (LED). Its turnover frequency reaches 392 h-1, not only better than homogeneous catalyst [Ru(bpy)3]Cl2 but also much superior those achieved over most reported heterogeneous catalysts. Moreover, it shows wide generality various aromatic amines, accompanied advantages good recyclability stability. mechanism corresponding polyoxometalate-based was fully investigated.

Language: Английский

Citations

20

A nickel/organoboron catalyzed metallaphotoredox platform for C(sp2)–P and C(sp2)–S bond construction DOI
Yuan Zhu,

Weisai Zu,

Qing Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(4), P. 1070 - 1076

Published: Jan. 1, 2022

A boron-based organic photocatalyst has been applied in metallaphotoredox catalyzed C–P and C–S bond construction reactions.

Language: Английский

Citations

17

A visible-light-induced bromine radical initiates direct C–H alkylation of heteroaromatics DOI

Xiangxue Cao,

Lanfeng Wei,

Jinbo Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1157 - 1161

Published: Jan. 1, 2024

Herein, a photoinduced direct C(sp 2 )–H alkylation of N -heteroaromatics by using commercially available tetrabutylammonium tribromide (TBATB) as HAT reagent is described.

Language: Английский

Citations

4

Transition metal-free visible light-mediated photocatalytic aerobic oxidative synthesis of N-heterocycles using molecular oxygen as an oxidant DOI
Yongke Hu,

Hongyou Tian,

Haotian Cao

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 566, P. 114432 - 114432

Published: Aug. 9, 2024

Language: Английский

Citations

4

Visible Light-Induced Aerobic Oxidative Dehydrogenation of C–N/C–O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments DOI Creative Commons
Alejandro Torregrosa-Chinillach, Rafael Chinchílla

Molecules, Journal Year: 2022, Volume and Issue: 27(2), P. 497 - 497

Published: Jan. 13, 2022

Performing synthetic transformation using visible light as energy source, in the presence of a photocatalyst promoter, is currently high interest, and oxidation reactions carried out under these conditions oxygen final oxidant are particularly convenient from an environmental point view. This review summarizes recent developments achieved oxidative dehydrogenation C–N C–O bonds, leading to C=N C=O respectively, air or pure metal-free homogeneous recyclable heterogeneous photocatalysts irradiation.

Language: Английский

Citations

15

Phenalenyl-Based Photocatalyst for Bioinspired Oxidative Dehydrogenation of N-Heterocycles and Benzyl Alcohols DOI
Vishali Pathania, Sudipta Raha Roy

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4145 - 4155

Published: Feb. 28, 2024

The environmental benefits of molecular oxygen as the oxidizing agent in oxidation reactions that synthesize fine chemicals cannot be overstated. Increased interest developing robust photocatalysts is stimulated by fact current photocatalytic transformation boom has made previously inaccessible synthetic approaches possible. Motivated enzymatic catalysis, employing a reusable phenalenyl-based photocatalyst, we have successfully developed oxidative dehydrogenation utilizing greener oxidant. Under photoinduced conditions, different types saturated N-heterocycles and alcohols were dehydrogenated. versatility this bioinspired protocol demonstrated wide variety N-heteroaromatics, such quinoline, carbazole, quinoxaline, acridine, indole derivatives, well aldehydes ketones, synthesized. Detailed mechanistic studies validate proposed mechanism. Fluorescence lifetime CV experiments revealed crucial role water on efficiency reaction. present also provides chemoselectivity scalability, leading to superior results allowing for functionalization bioactive molecules at late stage sustainable manner.

Language: Английский

Citations

3