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

Tongyao Zhou,

Hang Chen, Yang Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(22), С. 15582 - 15597

Опубликована: Ноя. 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.

Язык: 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

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(49), С. 6050 - 6053

Опубликована: Янв. 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.

Язык: Английский

Процитировано

62

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

и другие.

Organic Letters, Год журнала: 2023, Номер 25(11), С. 1994 - 1998

Опубликована: Март 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.

Язык: Английский

Процитировано

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

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(21), С. 2958 - 2961

Опубликована: Янв. 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.

Язык: Английский

Процитировано

10

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

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Май 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 1020 - 1026

Опубликована: Март 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

Язык: Английский

Процитировано

17

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4947 - 4957

Опубликована: Март 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.

Язык: Английский

Процитировано

8

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(4), С. 635 - 697

Опубликована: Янв. 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.

Язык: Английский

Процитировано

7

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

Qitao Shen,

Xiangyun Zheng, Lianghao Li

и другие.

Organic Letters, Год журнала: 2022, Номер 24(13), С. 2556 - 2561

Опубликована: Март 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.

Язык: Английский

Процитировано

24

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

Fangqi Shen,

Gaofeng Feng

и другие.

Organic Letters, Год журнала: 2021, Номер 23(10), С. 3913 - 3918

Опубликована: Апрель 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.

Язык: Английский

Процитировано

30

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

и другие.

Organic Letters, Год журнала: 2021, Номер 23(24), С. 9474 - 9479

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

29