Visible-light-induced three component difluoromethylation cyclization carbo-thioesterification to CF2-Containing γ-Lactams DOI

Dan Shao,

Tingting Yu,

Lianglong Sun

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 570, P. 114685 - 114685

Published: Nov. 21, 2024

Language: Английский

Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1H)-ones via polysulfide anion photocatalysis DOI
Zhongyi Zhang, Yaqin Zhou, Jiehui Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(8), P. 1708 - 1713

Published: Jan. 1, 2024

A visible-light-induced radical relay cyclization/C-C bond formation of quinoxalin-2(1

Language: Английский

Citations

26

Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances DOI Open Access
Keli Wang,

Hong‐Tao Ji,

Li‐Juan Ou

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 11, 2023

Abstract The multicomponent reactions of quinoxalin‐2(1 H )‐ones has attracted considerable interest due to their significant biological and chemical activities. very recent advances (from 2021 the beginning 2023) on radical three‐component cascade reaction )‐one derivatives at C3 position were summarized in this mini‐review. According kind types involved, some representative examples detailed mechanism have been categorized discussed. red front was covered by Figure 1.

Language: Английский

Citations

36

Copper-Catalyzed Radical Relay 1,3-Carbocarbonylation across Two Distinct C═C Bonds DOI

Nan‐Nan Dai,

Yue-Jiao Lu,

Zhong-Qi Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3014 - 3019

Published: March 28, 2024

The radical relay provides an effective paradigm for intermolecular assembly to achieve functionalization across remote chemical bonds. Herein, we report the first 1,3-carbocarbonylation of α-carbonyl alkyl bromides two separate C═C reaction is highly chemo- and regioselective, with C(sp3)–C(sp3) bonds one C═O bond formed in a single orchestrated operation. In addition, synthesis method under mild conditions using inexpensive copper as catalyst allows facile access structurally diverse products. plausible mechanism investigated through series control experiments, including trapping, clock critical intermediate 18O labeling experiment.

Language: Английский

Citations

12

Visible‐Light‐Driven Cyclizations DOI Creative Commons
Emilia Oueis, Mirella Elkadi, Ramón Rios

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 635 - 697

Published: Jan. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Language: Английский

Citations

7

Photoinduced Three-Component Difluoroamidosulfonylation/Bicyclization: A Route to Dihydrobenzofuran Derivatives DOI

Qitao Shen,

Xiangyun Zheng, Lianghao Li

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2556 - 2561

Published: March 29, 2022

A visible-light-induced photocatalyst-free three-component radical cascade bicyclization has been achieved to obtain diverse difluoroamidosulfonylated dihydrobenzofurans in moderate good yields. This protocol avoids potential toxicity and the tedious removal procedure for photocatalysts also features mild reaction conditions a functional group tolerance. Moreover, mechanistic investigations reveal formation of charge-transfer complex involvement an intramolecular 1,5-hydrogen atom transfer process this transformation.

Language: Английский

Citations

23

Visible-Light-Promoted Deoxygenative Alkylation of Quinoxalin-2(1H)-ones with Activated Alcohols DOI

Lili Wang,

Pengyuan Yang, Jinwei Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6334 - 6344

Published: April 15, 2024

A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.

Language: Английский

Citations

5

Iron-catalyzed methylation of quinoxalin-2(1H)-ones with dimethyl sulfoxide under visible light irradiation DOI
Hong He, Zhongyi Zhang,

Yicheng Zhang

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 558, P. 113999 - 113999

Published: March 11, 2024

Language: Английский

Citations

4

Recent Advances in Visible‐Light‐Enabled C3‐H Fluoroalkylation of Quinoxalin‐2(1H)‐ones DOI
Dong Ma, Xiaoxiang Wu, Tiebo Xiao

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(12)

Published: March 1, 2025

Abstract In light of the extensive application fluoroalkyl‐containing molecules and functionalized quinoxalin‐2(1 H )‐ones in medicinal chemistry functional materials, visible‐light‐enabled C3‐H fluoroalkylation has garnered significant attention. this review, we provide a detailed overview latest advancements rapidly evolving research area. We cover utilization various fluoroalkyl sources under conditions photocatalyst or without photocatalyst, discuss pertinent reaction conditions, mechanisms, substrate scope. Our objective is to help more chemists comprehend challenges opportunities within field, thereby fostering its development.

Language: Английский

Citations

0

Photoinduced Three‐Component Difluoroamidosulfonylation/Bicyclization: Regioselectivity Synthesis of Seven‐Membered Dibenzosultams DOI
Xiangyun Zheng,

Qitao Shen,

Chuanliu Yin

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(10), P. 1750 - 1756

Published: April 1, 2022

Abstract A mild and safe photochemical methodology has been developed to access difluoroamidosulfonylated dioxodibenzothiazepines via three‐component radical bicyclization cascades. This photocatalyst‐free transformation avoids cumbersome photocatalyst removal procedure potential toxicity. Mechanistic experiments reveal the generation of an electron donor‐acceptor (EDA) complex in reaction process. Moreover, synthetic value protocol is further demonstrated by gram‐scale reaction, conversion product total synthesis antidepressant drug. magnified image

Language: Английский

Citations

15

Photoinduced tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinoxalin-2(1H)-ones or coumarins under metal- and photocatalyst-free conditions DOI
Wei Zhao,

Liangming Xuan,

Yang Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(22), P. 10744 - 10750

Published: Jan. 1, 2023

A photocatalyst-free visible-light-promoted tandem intramolecular cyclization/heteroarylation between bromodifluoroacetamides and quinoxalin-2(1 H )-ones or coumarins was developed. The process could generate a broad range of α , -difluoro-γ-lactams.

Language: Английский

Citations

8