Mn(acac)3/Hydrazide-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Couplings of 1,2,3,4-Tetrahydroisoquinolines and Their Mechanistic Studies DOI

Ga Young Kim,

S.-Y. Park,

Gayeong Park

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 20, 2025

Aerobic oxidative cross-dehydrogenative couplings of 1,2,3,4-tetrahydroisoquinolines were developed using a Mn(acac)3 and ethyl 2-(4-nitrophenyl)hydrazine-1-carboxylate cocatalytic system. Nucleophiles, including nitroalkanes, dialkyl malonates, acetophenones, indoles, phosphonates, phosphine oxides, successfully employed to produce α-functionalized 1,2,3,4-tetrahydroisoquinolines. Control experiments revealed that radical species are not involved in the mechanism. Additionally, 1H NMR HRMS analyses stoichiometric reaction identified an aminal structure as crucial intermediate. Computational studies further support plausibility hydride transfer process oxidation instead triazane pathway, which was predominantly proposed DEAD-mediated reaction.

Language: Английский

Copper-doped carbon nitride as a practical heterogeneous metallaphotocatalyst for aerobic oxidative cross-coupling of tertiary amines with terminal alkynes DOI
Yilian Bai, Qian Yang, Yurong Tang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(11), P. 4446 - 4452

Published: Jan. 1, 2023

A Cu-doped carbon nitride-based heterogeneous metallaphotocatalytic α-alkynylation of tertiary amines has been developed, allowing for green and sustainable synthesis diverse valuable propargylamines with high efficiency.

Language: Английский

Citations

19

Dual Molecular Oxygen Activation Sites on Conjugated Microporous Polymers for Enhanced Photocatalytic Formation of Benzothiazoles DOI
Sizhe Li, Jie Yin, Hao Zhang

et al.

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(2), P. 2825 - 2831

Published: Jan. 4, 2023

Oxidative formation of high value compounds involving active oxygen species using heterogeneous polymeric photocatalysts has become a useful tool in catalysis. Controlling the interaction between sites on polymer and molecules is still challenging due to rather large backbone structure. Here, we design triazine-containing donor acceptor-type conjugated microporous (CMP) containing dual major at F N atoms for molecular activation. Introducing fluorine CMP led combined effect enhanced adsorption electron transfer oxygen. Time-resolved photoluminescence, electronic paramagnetic resonance spectra, DFT calculation revealed favorable absorption energy kinetics molecules, thus efficiently generating superoxide radicals (O2•-) singlet (1O2) as main species. The photocatalytic activity, selectivity, reusability was demonstrated by variety benzothiazoles.

Language: Английский

Citations

18

Redox-Active Organic Materials: From Energy Storage to Redox Catalysis DOI Creative Commons
Jaehwan Kim, Jianheng Ling,

Yihuan Lai

et al.

ACS Materials Au, Journal Year: 2024, Volume and Issue: 4(3), P. 258 - 273

Published: Jan. 12, 2024

Electroactive materials are central to myriad applications, including energy storage, sensing, and catalysis. Compared traditional inorganic electrode materials, redox-active organic such as porous polymers (POPs) covalent frameworks (COFs) emerging promising alternatives due their structural tunability, flexibility, sustainability, compatibility with a range of electrolytes. Herein, we discuss the challenges opportunities available for use in organoelectrochemistry, an area fine chemical synthesis. In particular, highlight utility photoredox catalysis, electrochemical electrocatalysis point new directions needed unlock potential This Perspective aims bring together organic, electrochemistry, polymer communities design heterogeneous electrocatalysts sustainable synthesis complex molecules.

Language: Английский

Citations

7

A review on photocatalysis and nanocatalysts for advanced organic synthesis DOI Creative Commons
Jyoti Bhattacharjee, Subhasis Roy

Hybrid Advances, Journal Year: 2024, Volume and Issue: 6, P. 100268 - 100268

Published: Aug. 1, 2024

Control of redox processes at the molecular level is central to synthesis, and electrochemistry provides a unique means directing electron flow for chemical transformations. Although chemistry community has long recognized its power, potential electrochemical methods in organic synthesis not been nearly as exploited academically or industrially. In this respect, review related applying nano-photocatalysts fine producing compounds presented. The existing laboratory industrial are too resource-intensive, mostly based on non-renewable energy sources, often require extreme conditions regarding temperature pressure. review, we emphasize forward transformations realizable with help such nanomaterials under UV/visible light exposure. Nanophotocatalysts thus offer huge green high-value-added organics. This outlines organics nanophotocatalysts, graphene semiconductors, titanium oxide, quantum dots, carbon-based catalysts. aims present current research field provide an impetus helpers further build area social impact. For first time, all-inclusive approach helps bridge gaps between these different areas view challenges electro-organic photocatalysis.

Language: Английский

Citations

7

Controlled synthesis of Cadmium doped CuBi2O4 nanorods with rapid and synergistic visible light photocatalytic performance DOI
Javed Ali Khan, Afaq Ullah Khan, Younas Khan

et al.

Chemical Engineering Science, Journal Year: 2024, Volume and Issue: 293, P. 120025 - 120025

Published: March 19, 2024

Language: Английский

Citations

6

Thermally Activated Delayed Fluorescence Sensitizers As Organic and Green Alternatives in Energy-Transfer Photocatalysis DOI
Ryoga Hojo,

Alexander M. Polgar,

Zachary M. Hudson

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(30), P. 9665 - 9678

Published: July 21, 2022

Photocatalysis has captured the imagination of synthetic chemists and is poised to become a staple fine chemical industry. Over past decade, subfield energy-transfer (EnT) catalysis expanded dramatically, harnessing excited states photosensitizer unlock variety redox-neutral, radical-based reactivities in mild selective fashion. However, many developments this discipline rely on precious rare earth metals such as iridium. This perspective will highlight rise thermally activated delayed fluorescence (TADF) materials metal-free alternatives EnT photocatalysis for organic transformations. Emphasis be placed recent progress cycloadditions, E/Z isomerization olefins, other radical-initiated processes; all mediated by mechanism Dexter energy transfer. The tunable excited-state energetics dynamics TADF allow them effectively compete with iridium-based sensitizers, indicating their promise green organocatalysis.

Language: Английский

Citations

27

Enhanced efficiency of interfacial charge transfer in Ag3PO4/BiPO4@CNTs photocatalyst for amoxicillin degradation: Synergistic effect of p-n heterojunction and conjugated channels DOI
Yadong Wu, Yongxin Luo,

Chaoseng Yang

et al.

Surfaces and Interfaces, Journal Year: 2024, Volume and Issue: 51, P. 104801 - 104801

Published: July 14, 2024

Language: Английский

Citations

5

Embracing Heterogeneous Photocatalysis: Evolution of Photocatalysts in Annulation of Dimethylanilines and Maleimides DOI
Yan Liu, Rui Li, Qi‐Yan Lv

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(66), P. 8645 - 8657

Published: Jan. 1, 2024

Recent advances in visible-light-promoted construction of tetrahydroquinolines from dimethylanilines and maleimides are documented. Homogeneous heterogeneous photocatalytic systems, as well the reaction mechanism, emphasized. The mechanism this annulation is quite clear,

Language: Английский

Citations

5

Visible-Light-Promoted Phosphorylation/Cyclization of 1-Acryloyl-2-cyanoindoles in Green Solvent DOI
Anxiang Huang,

Yi-Rui Fu,

Hu-Lin Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14433 - 14442

Published: Oct. 18, 2022

A visible-light-induced persulfate-promoted cascade phosphorylation/cyclization reaction to access various phosphorylated pyrrolo[1,2-a]indolediones under mild conditions was developed. Notably, the transformation carried out with diethyl carbonate/H2O as a green medium at room temperature. More impressively, traditional metal catalysts and photocatalysts could be effectively avoided. The reactions are simple operate, easy scale up, have good functional group tolerance.

Language: Английский

Citations

22

1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN)-based porous organic polymers for visible-light-driven organic transformations in water under aerobic oxidation DOI

Shan‐Shan Zhu,

Lin Zuo,

Yan Liu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(22), P. 8725 - 8732

Published: Jan. 1, 2022

A series of hyper-crosslinked POPs were constructed by Friedel–Crafts alkylation reaction 4CzIPN with FDA, which contains a certain quantity hydrophilic ether residues to facilitate visible-light-promoted aqueous organic transformations.

Language: Английский

Citations

21