A Benzophenothiazine/Boronic Acid Hybrid Photocatalyst Enables the Single Electron Transfer (SET) to Carboxy Groups: SET-Initiated Cyclization of α,β-Unsaturated Carboxylic Acids DOI

Taichi Yumura,

Takeshi Nanjo, Yoshiji Takemoto

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 12803 - 12809

Published: Sept. 18, 2023

In this article, we report an efficient hybrid photoredox catalyst that combines N-arylbenzophenothiazine and a boronic acid. The forms complex with the substrate to enable single electron reduction of redox-inactive carboxy groups under visible-light irradiation. Via approach, two types radical cyclization α,β-unsaturated carboxylic acids previously required harsh reaction conditions can be achieved, i.e., [2 + 2] cycloaddition reductive cyclization. Mechanistic studies have revealed photocatalyst promotes transfer toward generally unreactive cyclobutane acid moieties adducts as well acids, leading unusual cis–trans isomerization rings via reversible ring-opening/-closing process.

Language: Английский

Decatungstate-Photocatalyzed Transfer Hydrogenation of Alkenes Using Alcohol as the Hydrogen Source DOI
Cheuk‐Wai So, Teng Zhang, Zhengfeng Zhang

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: May 14, 2025

Abstract We present a simple and efficient photocatalytic method for the transfer hydrogenation of alkenes alkynes using alcohol as hydrogen source inexpensive decatungstate photocatalyst. Our approach operates under mild, ambient conditions demonstrates broad substrate compatibility, accommodating alkyl, aryl, heteroatom-substituted alkynes. To our knowledge, this study represents first instance tungsten-based catalysts alkenes. Notably, decatungstate/alcohol catalytic system exhibits excellent chemoselectivity, enabling selective even in presence reactive groups like ketones carboxylic acids. These features highlight considerable potential practical sustainable applications organic synthesis.

Language: Английский

Citations

0

Thioxanthone-based ionic liquid as photocatalyst for a tandem cyclization reaction to synthesize pyrroloquinolinones DOI

Huixin Tong,

Mengqi Zou,

Yuli Sha

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2024, Volume and Issue: 348, P. 123835 - 123835

Published: April 24, 2024

Language: Английский

Citations

3

Electricity-driven organic hydrogenation using water as the hydrogen source DOI Creative Commons
Bidyut Kumar Kundu, Yujie Sun

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Employing water as a hydrogen source is an attractive and sustainable option in electricity-driven organic hydrogenation, which can overcome the drawbacks associated with traditional sources like H 2 .

Language: Английский

Citations

3

A MOF-based array sensor for the differential detection of nitroaromatic compound isomers. DOI
Zixuan Zhou, Yu-Han Jiang, Xin Luo

et al.

Applied Materials Today, Journal Year: 2024, Volume and Issue: 42, P. 102557 - 102557

Published: Dec. 19, 2024

Language: Английский

Citations

3

Organophotocatalytic Alkene Reduction Using Water as a Hydrogen Donor DOI
Wenjie Kang, Yuze Pan, Aishun Ding

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7633 - 7638

Published: Oct. 16, 2023

The chemical activation and functionalization of water are considered an ideal method for converting earth-abundant sources into valuable chemicals. Here, we show that a non-activated free molecule can be applied directly as hydrogen donor to achieve the carbanion-mediated alkene reduction with 9-HTXTF serving organophotocatalyst. Notably, direct syntheses high-value-added drugs bioactive molecules readily achieved by utilizing plentiful energy resource, showcasing usefulness protocol in synthesis.

Language: Английский

Citations

7

Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission DOI Open Access

Vikas Dixit,

Pooja Sharma, Nidhi Jain

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4684 - 4691

Published: Nov. 11, 2023

Abstract We demonstrate a photocatalyst and transition metal catalyst free photo‐activation of quinoxalin‐2(1 H )‐ones in visible light the presence an acid catalyst. The photoactivated )‐one species transfers its energy to oxygen which promotes C−N cross dehydrogenative coupling with nucleophilic partners such as carbazoles, azoles amides giving products 42–75% yields. Preliminary studies reveal )‐one‐carbazole adducts display fluorescent properties including Intramolecular Charge Transfer (ICT) Aggregate Induced Emission (AIE).

Language: Английский

Citations

7

Visible Light-Induced Regioselective Intermolecular [2 + 2]-Cycloaddition of Alkyne and 2(1H)-Quinolone Derivatives DOI
Hai Hao,

Shaoheng Qin,

Yanzhi Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1353 - 1360

Published: Jan. 8, 2024

We have developed a visible light-induced intermolecular [2 + 2]-cycloaddition reaction between alkenes and alkynes using thioxanthone Cu(OTf)2 as cocatalysts. Various quinolin-2(1H)-ones, featuring diverse substituted groups, were successfully employed in this reaction, resulting the synthesis of series 4,8b-dihydrocyclobuta[c]quinolin-3(2aH)-ones. Our methodology presents novel synthetic approach for alkene-alkyne 2]-cycloaddition, delivering cyclobutene derivatives with exceptional regioselectivity.

Language: Английский

Citations

2

Thioxanthone-TfOH complex (9-HTXTF) photoredox enabled reduction of sulfoxides DOI
B.‐C. CHEN, Jiayi Wang, Weiqiang Sun

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 139, P. 155007 - 155007

Published: March 15, 2024

Language: Английский

Citations

2

Aluminum-Catalyzed Intramolecular Vinylation of Arenes by Vinyl Cations DOI
Wenhua Lin, Aurélien Alix, Régis Guillot

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3267 - 3272

Published: April 4, 2024

This study addresses the challenges associated with vinyl cation generation, a process that traditionally requires quite specific counterions. Described herein is novel intramolecular vinylation of arenes catalyzed by aluminum(III) chloride, utilizing practical conditions and readily available triflates derived from 2-aceto-3-arylpropionates. Comprehensive experimental data support diverse carbocycle synthesis, exemplified indenes higher analogues. Control experiments verify applicability protocol, synthetic applications showcase potent tubulin polymerization inhibitor anticancer properties. Density functional theory computations reveal Lewis-acid-driven mechanism involving triflate moiety abstraction to generate reactive cation.

Language: Английский

Citations

2

Photoredox-catalyzed hydrogenation of alkenes assisted by an in situ generated PPh3(OH) radical and acetic acid DOI
Zhenzhen Xie, Yu Zheng,

Zi‐Hao Liao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4187 - 4193

Published: Jan. 1, 2024

Herein, a practical, mild and convenient strategy was disclosed for the hydrogenation of alkenes under photocatalytic conditions through HAT/protonation process.

Language: Английский

Citations

2