Visible Light‐Induced Umpolung Synthesis of 3,3‐Disubstituted Oxindoles via the Substrate‐Photosensitive Strategy DOI
H. J. Yang, Ting-Ting Wang,

Benhui Sui

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Comprehensive Summary 3,3‐Disubstituted oxindoles, forming the core of extensive bioactive natural products and drugs, attract tremendous efforts to develop efficient methods for their preparation. Here, a photocatalyst‐free approach synthesis 3,3‐disubstituted oxindoles via substrate‐photosensitive strategy under visible light was successfully developed. Preliminary mechanistic studies illustrated that isatin‐derived imines can be directly excited by generate strong oxidant states, facilitating subsequent single‐electron transfer (SET) processes with Hantzsch esters afford corresponding α‐amino radical intermediates. Thus, these radicals promote Giese addition or radical/radical cross‐coupling reactions furnish diverse functionalized 3‐substituted 3‐aminooxindoles in high yields.

Language: Английский

Electroreduction strategy: a sustainable tool for the generation of aryl radicals DOI
Xiaoqing Xie,

Wei Zhou,

Ruchun Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4318 - 4342

Published: Jan. 1, 2024

This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.

Language: Английский

Citations

9
The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

Citations

9
Metal-Free, Visible-Light-Mediated Synthesis of Tetracyclic Benzimidazole: Regioselective C–H Functionalization with In Vitro and Computational Study of Anti-breast Cancer Compounds DOI Creative Commons
Anita Choudhary,

Nachiket Dattatray Garge,

Ala Chandu

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(6), P. 5778 - 5794

Published: Feb. 3, 2025

Globally, breast cancer is the leading cause of mortality. Within field antibreast drug design by several compound docking studies, eight new N-containing nonsteroid tetracyclic derivatives have been synthesized via regioselective intramolecular C-H functionalization visible light. The adopted methodology highly efficient, green, and sustainable to unload a pathway with excellent yield. It offers rapid, low-cost, catalyst-free method for creating physiologically active molecules from easily accessible substrates. substances were described using spectroscopic methods like HRMS, 1HNMR, 13CNMR, XRD analysis. This study explores cytotoxic potential novel compounds against human MCF-7 cells. includes in vitro experiments assess effect our on These include cytotoxicity assessment cell cycle, apoptosis, MTT test analysis flow cytometry, reactive oxygen species (ROS) production assessment, etc. Among compounds, 2e exhibited most potent activity, an inhibitory concentration (IC50) 40 nM, surpassing efficacy established drugs such as exemestane (IC50 24.97 micromolar) tamoxifen 5.45 μM). Compound also significantly induced apoptosis cycle arrest G1 phase, increasing apoptotic population 65.97%. Additionally, led marked rise level ROS generation, implicating oxidative stress its mechanism action. Molecular dynamic simulation further supported vigorous anticancer activity 2e, demonstrating promise effective treatment.

Language: Английский

Citations

1
Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(18), P. 5143 - 5160

Published: Jan. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Language: Английский

Citations

3
Dual Ligand Enabled Pd-Catalyzed Ortho-Alkylation of Iodoarenes DOI
Xiaoxia Wang, Lei Jiao

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(37), P. 25552 - 25561

Published: Sept. 5, 2024

The synthesis of complex polysubstituted aromatic molecules from simple precursors is a central goal in organic chemistry. In this study, we developed an approach for the

Language: Английский

Citations

2
Dual Ligand Enabled Pd-Catalyzed Ortho-Alkylation of Iodoarenes DOI Creative Commons
X.J. Wang, Lei Jiao

Published: May 10, 2024

The synthesis of complex polysubstituted aromatic molecules from simple precursors is a central goal in organic chemistry. In this study, we developed an approach for the ortho-alkylation iodoarenes utilizing dual ligand catalytic system. By combining Pd/olefin cooperative catalysis with bulky trialkylphosphine ligand-promoted C(sp2)-I reductive elimination, have established ortho-alkylative Catellani-type reaction aryl-iodine bond reconstruction as final step, which opens new synthetic opportunities within reactions. Through in-depth mechanistic investigations, isolated and characterized key organopalladium intermediates, revealing synergistic interaction ligands merging process elimination. present study showcases unique advantages emphasizes effectiveness system expanding chemical space Catellani

Language: Английский

Citations

1
Late-stage functionalization using a popular titrating agent: aryl- chlorides and -fluorides activation by the diphenylacetic acid dianion DOI Creative Commons

Alessandro Cerveri,

Giulia Russo, Sara Sparascio

et al.

Published: Aug. 8, 2024

Aryl-chlorides and -fluorides are common building blocks, but their use in synthesis is limited by the high stability of Ar-X bonds. The generation aryl radicals via activation strong bonds possible through irradiation tailor-made organic anions, which become reductants stronger than lithium metal. We report that combination visible light with cheap diphenylacetic acid dianion an even better tool, showing excellent activity across a variety complex substrates providing opportunities for late-stage drug modification. chemoselectively activated presence more easily reducible functions, such as Alk-Cl ones carbonyl groups, reminding Marcus inverted region principle. These results pave way to original synthetic strategies would be otherwise considered impossible

Language: Английский

Citations

1
Visible-light-induced decarboxylative cyclization DOI
Suven Das

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

The present review focuses on recent progress (2020–2024) in the visible-light-driven decarboxylative cyclization of various carboxylic acid derivatives for constructing carbo-/heterocycles.

Language: Английский

Citations

1
I2-Mediated [3 + 3] Annulation for the Construction of Indole-Pyrimidine-Pyrazole-Fused Tetracyclic Heteroarenes DOI

Heng-Tong Qu,

Long-Sheng Zhou,

Jiaxin Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15164 - 15169

Published: Oct. 7, 2024

An I2-mediated annulation of 3-aminopyrazoles with indole-3-carboxaldehydes has been demonstrated for the first time. This tandem strategy allows facile construction indole-pyrimidine-pyrazole-fused tetracyclic heteroarenes that are otherwise inaccessible by existing methods. These fused heterocycles exhibited enhanced antifungal activities against Valsa mali and Botryosphaeria dothidea compared commercial Xemium fungicide.

Language: Английский

Citations

0
Late‐stage Functionalization using a Popular Titrating Agent: Aryl‐Chlorides and ‐Fluorides Activation by the Diphenylacetic Acid Dianion DOI Creative Commons

Alessandro Cerveri,

Giulia Russo, Sara Sparascio

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Oct. 27, 2024

Abstract Aryl‐chlorides and ‐fluorides are common building blocks, but their use in synthesis is limited by the high stability of Ar−X bonds. The generation aryl radicals via activation strong bonds possible through irradiation tailor‐made organic anions, which become reductants stronger than lithium metal. We report that combination visible light with cheap diphenylacetic acid dianion an even better tool, showing excellent activity across a variety complex substrates providing opportunities for late‐stage drug modification. chemoselectively activated presence more easily reducible functions, such as Alk‐Cl ones carbonyl groups. These results pave way to original synthetic strategies would be otherwise considered impossible.

Language: Английский

Citations

0