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

Ambient Preparation of Benzoxazine‐based Phenolic Resins Enables Long‐term Sustainable Photosynthesis of Hydrogen Peroxide DOI Creative Commons
Xinyao Wang, Xiaowei Yang, Chen Zhao

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(23)

Published: March 25, 2023

Rational design of polymer structures at the molecular level promotes iteration high-performance photocatalyst for sustainable photocatalytic hydrogen peroxide (H2 O2 ) production from oxygen and water, which also lays basis revealing reaction mechanism. Here we report a benzoxazine-based m-aminophenol-formaldehyde resin (APFac) polymerized ambient conditions, exhibiting superior H2 yield long-term stability to most polymeric photocatalysts. Benzoxazine structure was identified as crucial active segment in APFac. Favorable adsorption oxygen/intermediates on benzoxazine commendable product selectivity accelerated kinetically stepwise single-electron reduction reaction. The proposed phenolic provides possibility batches industrial application, sheds light de novo analysis metal-free

Language: Английский

Citations

76

Triazine Frameworks for the Photocatalytic Selective Oxidation of Toluene DOI Creative Commons
Sizhe Li,

Niklas Huber,

Wei Huang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(18)

Published: Feb. 26, 2024

Investigations into the selective oxidation of inert sp

Language: Английский

Citations

22

Rational Design of 3D Space Connected Donor–Acceptor System in Covalent Organic Frameworks for Enhanced Photocatalytic Performance DOI

Yinghui Xie,

Fengyi Mao,

Qiuyu Rong

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: 34(52)

Published: Aug. 27, 2024

Abstract Herein, a rational strategy is presented to reduce the energy barrier of singlet ground state excited transitions, whilst simultaneously reducing losses in populating triplet states. The approach relies on constructing 3D space connected donor–acceptor systems COFs. D–A system 8‐connected COFs (denoted as COF‐1 and COF‐2) allows efficient transfer electrons, overcoming traditional electron transport limitations 2D significantly boosting solar utilization efficiency under visible light irradiation. COF‐2, possessing an extended π‐conjugated structure relative COF‐1, demonstrated high selectivity for photocatalytic generation H 2 O (6.93 mmol g −1 h ) natural seawater without need sacrificial reagents, exceeding performance most previously reported COF‐based photocatalysts. this work offers new optimizing photocatalysts production other applications.

Language: Английский

Citations

19

Oxamic acids: useful precursors of carbamoyl radicals DOI Creative Commons
Ikechukwu Martin Ogbu, Gülbin Kurtay, Frédéric Robert

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(55), P. 7593 - 7607

Published: Jan. 1, 2022

Thermal, photochemical, or electrochemical-mediated decarboxylation of oxamic acids generate nucleophilic carbamoyl radicals, which react efficiently with unsaturated systems, but also amines, alcohols and thiols under oxidative conditions.

Language: Английский

Citations

44

Photocatalytic H2O2 production from resorcinol-formaldehyde resin spheres with anthraquinone structure DOI
Liang Feng, Liang Zhou, Lingzhi Wang

et al.

Separation and Purification Technology, Journal Year: 2024, Volume and Issue: 338, P. 126527 - 126527

Published: Jan. 27, 2024

Language: Английский

Citations

11

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024 DOI
Martha C. Mayorquín‐Torres, Andreas Simoens, Eli Bonneure

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(12), P. 7907 - 7975

Published: May 29, 2024

The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search development synthetic routes for obtaining novel members this family compounds. This updated review covers methodologies established since 2004, focusing on synthesis phosphonates, which phosphonate moiety is directly substituted onto to structure. Emphasizing recent advances, classifies newly developed approaches according ring size providing information biological activities whenever available. Furthermore, summarizes various methods formation C–P bonds, examining sustainable such as Michaelis–Arbuzov reaction, Michaelis–Becker Pudovik Hirao coupling, Kabachnik–Fields reaction. After analyzing applications investigated years, a predominant focus evaluation these compounds anticancer agents evident. emerging underline versatility potential compounds, highlighting need continued research expand interesting family.

Language: Английский

Citations

11

5,12-Dihydroquinoxalino[2,3-b] quinoxaline-based porous organic polymer as photocatalyst for visible-light-driven cross-coupling reactions DOI

Shui-Li Liu,

Yifei Zhang, Peng Qin

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 115972 - 115972

Published: Jan. 1, 2025

Language: Английский

Citations

1

N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines DOI

Shengjie Song,

Wenjian Wang,

Yali He

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Herein, a N-phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this demonstrates outstanding stability, extensive surface area, exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency recyclability in the photochemically driven difluoromethylation/cyclization reactions. This work provides strategy design construction of photocatalysts offers support their broad prospects synthetic applications.

Language: Английский

Citations

1

Access to Phosphine-Containing Quinazolinones Enabled by Photo-Induced Radical Phosphorylation/Cyclization of Unactivated Alkenes DOI

Binsong Mu,

Le Zhang,

Guanghui Lv

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 10146 - 10157

Published: July 13, 2022

A mild and facile photo-induced cascade radical addition/cyclization of unactivated alkenes has been reported, through which a variety biologically valuable phosphine-containing quinazolinones could be obtained in moderate to good yields. The protocol was characterized by conditions, broad substrate scope, high atomic economy.

Language: Английский

Citations

29

Bismuth vanadate: A versatile heterogeneous catalyst for photocatalytic functionalization of C(sp2)–H bonds DOI

Fan‐Lin Zeng,

Hu-Lin Zhu,

Ru-Nan Wang

et al.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2023, Volume and Issue: 46, P. 157 - 166

Published: Feb. 23, 2023

Language: Английский

Citations

21