Visible-Light-Promoted Xanthate-Transfer Cyclization Reactions of Unactivated Olefins under Photocatalyst- and Additive-Free Conditions DOI

Tongyao Zhou,

Hang Chen, Yang Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15582 - 15597

Published: Nov. 1, 2022

A general visible-light-induced photocatalyst-/additive-free strategy was developed for the construction of various nitrogen-heterocycles (42 examples, up to 97% yield) such as γ-lactams, δ-lactams, pyrrolidines, indolones, quinolinones, and fused polycyclic structures at room temperature. The prominent features this protocol are mild environmentally friendly conditions, broad substrate scope, good functional group tolerance. Importantly, reaction can be performed under natural sunlight, most sustainable energy source imaginable. Furthermore, provides straightforward access a range derivatives through subsequent elaboration xanthate group.

Language: Английский

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives DOI
Bin Sun,

Rongcheng Shi,

Kesheng Zhang

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(49), P. 6050 - 6053

Published: Jan. 1, 2021

A green and efficient strategy for the synthesis of quinazolinone derivatives via photo-induced decarboxylative cascade radical acylation/cyclization unactivated alkenes has been developed under oxidant photocatalyst free conditions.

Language: Английский

Citations

62

α-Amino Radical-Mediated Difunctionalization of Alkenes with Polyhaloalkanes and N-Heteroarenes DOI
Jiabin Shen, Xiao‐Guang Yue, Jun Xu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(11), P. 1994 - 1998

Published: March 15, 2023

Herein, we report a mild and practical protocol for the α-perchloroalkyl β-heteroarylation of alkenes using available chloroform as dichloromethyl source via α-amino radical-mediated halogen-atom transfer. Various substrates are compatible under reaction conditions, providing corresponding products in moderate to good yields. This strategy gives an efficient convenient method introduction chloroalkyl motifs into N-heteroarenes. The control experiment demonstrates that radical generated situ is key intermediate transformation.

Language: Английский

Citations

34

Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones DOI

Dong‐Liang Zhang,

Zhanggao Le,

Qing Li

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(21), P. 2958 - 2961

Published: Jan. 1, 2024

Visible-light-driven EDA complex-promoted ring-opening of cycloketone oxime esters to synthesise various 4-cyanoalkylated isoquinoline-1,3-diones with acryloylbenzamides was developed.

Language: Английский

Citations

10

Direct Functionalization of para‐Quinones: A Historical Review and New Perspectives DOI
Raushan Kumar Jha, Sangit Kumar

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 21, 2024

Abstract The direct functionalization of quinones has always fascinated research communities due to their biological and redox activities subsequent application. Quinone motifs play a vital role as precursors for many bioactive compounds materials; hence, ingenious methodologies have been elaborated exploring these units. A significant part the synthetic strategies towards functionalized achieved by installing substituents on hydroquinones, phenols, or quinone itself different oxidative coupling reactions via radical pathways with without utilization metal catalysts. simple C−H bond remains challenging inherited electronic nature high dissociation energy. This review article summarizes recent advancement made through quinones. Our primary focus will be approaches mechanistic that appeared in last two decades, along short historical importance family.

Language: Английский

Citations

10

Visible‐Light‐Driven Multicomponent Radical Cascade Versatile Alkylation of Quinoxalinones Enabled by Electron Donor Acceptor Complex in Water DOI
Bin Sun, Xiaoli Tang,

Xiaohui Zhuang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1020 - 1026

Published: March 10, 2023

Abstract An operationally simple aqueous phase three‐component photochemical strategy for the alkylation of quinoxalin‐2(1 H )‐ones with diethyl α ‐bromomalonate and unactivated alkenes in absence both photoredox catalysts additive has been developed. This reaction is driven by activity electron donor‐acceptor (EDA) complexes formed ‐bromomalonate. Irradiation visible light triggered single‐electron transfer (SET) from to ‐bromomalonate, inducing formation corresponding alkyl radical subsequent tandem reaction. It provides an efficient way construct alkylated quinoxalinones small molecules. magnified image

Language: Английский

Citations

17

Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation DOI
Pengbo Zhang, Wenwu Li, Shuai Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4947 - 4957

Published: March 18, 2024

A photoredox/copper-catalyzed cascade radical cyclization/phosphorothiolation reaction of N-allylbromoacetamides and P(O)SH compounds has been established. broad range novel nonfluorine- or difluoro-substituted 2-pyrrolidinones bearing the C(sp3)-SP(O)(OR)2 moiety can be conveniently constructed in moderate to good yields under mild conditions. Importantly, most tested phosphorothiolated showed potent inhibitory effects toward both AChE BChE.

Language: Английский

Citations

8

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-Induced α-Amino C–H Bond Arylation Enabled by Electron Donor–Acceptor Complexes DOI
Chang Xu,

Fangqi Shen,

Gaofeng Feng

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(10), P. 3913 - 3918

Published: April 30, 2021

Enabled by electron donor–acceptor complexes, a novel visible-light-induced α-amino C–H bond arylation protocol, without photoredox catalyst, has been disclosed. The protocol does not require any transition metal, oxidant, or exclusion of oxygen moisture. A direct irradiation the mixture tertiary amines and benzonitriles with visible light in N,N-diethylethanamide presence Cs2CO3 afforded α-arylated good to excellent yields.

Language: Английский

Citations

30

Visible-Light-Promoted Hydroxydifluoroalkylation of Alkenes Enabled by Electron Donor–Acceptor Complex DOI
Zhenzhen Xie, Yu Zheng, Kai Tang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(24), P. 9474 - 9479

Published: Nov. 30, 2021

A catalyst-free strategy for regioselective hydroxydifluoroalkylation of alkenes with alkyl bromides was developed, affording a series difluoroalkylated tertiary alcohols in moderate to good yields. This photocatalyst-free protocol shows broad substrate scope under mild conditions. Moreover, mechanistic studies revealed that newly identified electron donor-acceptor complex is crucial this transformation.

Language: Английский

Citations

29