Transition‐Metal‐Free Radical Cyclization of 2‐Arylbenzoimidazoles with Unactivated AlkanesviaC(sp3)−H Functionalizations in Aqueous Media DOI

Jiao‐Zhe Li,

Lan Mei,

Xue‐Er Cai

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2080 - 2085

Published: May 6, 2022

Abstract Here we present a transition‐metal‐free radical cyclization of 2‐arylbenzoimidazoles with unactivated alkanes. By using di‐ tert ‐butyl peroxide (DTBP) to promote the C( sp 3 )−H bond functionalization, this approach enables assembly various benzimidazo[2,1‐ ]isoquinolin‐6(5 H )‐ones in aqueous media. This strategy can not only well tolerate wide range cyclic alkanes, straight‐chain toluene derivatives, as pharmaceutical molecule eudesmol, but also provides an for functionalization bonds media under systems. magnified image

Language: Английский

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes DOI
Lvyin Zheng,

Liuhuan Cai,

Kailiang Tao

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(4), P. 711 - 748

Published: Feb. 11, 2021

Abstract Photocatalyzed organic synthesis transformation is a remarkable green synthetic strategy because of the advantages operational simplicity, high chemoselectivities, cheap, and environmental benignancy, along with extensive applications in fields organic, pharmaceutical functional material chemistry. Generally, photoredox catalysts or photosensitizers are necessary for generation their excited states to perform successive oxidative reductive reactions through single electron transfer (SET) energy (ET) process. Furthermore, exploration colored donor‐acceptor (EDA) complex charge (CT) between an electron‐rich electron‐poor substrate provides chance deliver intermediate under irradiation light, resulting formation radical activate species induce various reactions. These were performed without need any external photocatalysts mild reaction conditions. Herein, this review focuses on recent progress photoinduced addition reactions, borylations, radical‐radical cross‐coupling degradation cascade cyclization via EDA complexes. We highlight these novel methodologies applications, as well mechanisms. This will help provide references medicinal chemists who charmed by photochemical transformations based

Language: Английский

Citations

110

Fluorination and fluoroalkylation of alkenes/alkynes to construct fluoro-containing heterocycles DOI
Xin Wang,

Lei Jia,

Yingjie Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(9), P. 2079 - 2109

Published: Jan. 1, 2021

This review summarize the established strategies through fluorination and fluoroalkylation of alkenes/alkynes for constructing fluoro-containing heterocycles. Reaction scopes, mechanisms some shortcomings are also discussed.

Language: Английский

Citations

79

Recyclable Perovskite as Heterogeneous Photocatalyst for Aminomethylation of Imidazo‐Fused Heterocycles DOI
Tao Shi, Kai Sun, Xiaolan Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(11), P. 2143 - 2149

Published: Jan. 8, 2020

Abstract A sustainable and cost‐effective protocol for direct aminomethylation of imidazo‐fused heterocycles by decarboxylative coupling reaction N ‐phenylglycines with in the presence CsPbBr 3 under irradiation visible light has been developed. This is first example ‐catalyzed heterocycles. The eminent advantage this work that, easily prepared can be used at least 5 times without obvious reduction its activity, exhibiting high catalyst economic feature. magnified image

Language: Английский

Citations

76

Metal-Free Photosynthesis of Alkylated Benzimidazo[2,1-a]isoquinoline-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones in PEG-200 DOI

Hao‐Cong Li,

Kai Sun, Xiang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(13), P. 9055 - 9066

Published: June 23, 2021

A visible-light-induced decarboxylation reaction was developed for the synthesis of alkylated benzimidazo[2,1-a]isoquinoline-6(5H)-ones and indolo[2,1-a]isoquinolin-6(5H)-ones under metal-free conditions. Impressively, metal catalysts traditionally volatile organic solvents could be effectively avoided.

Language: Английский

Citations

59

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions DOI
Jian-Qiang Chen,

Xiaodong Tu,

Binyan Qin

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 642 - 647

Published: Jan. 5, 2022

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It worth noting that method not only can afford the synthesis but also provide an alternative route for generating complex target structures bearing carboxylic esters.

Language: Английский

Citations

55

Radical Perfluoroalkylation of Aliphatic Substrates DOI
Damian E. Yerien, Sebastián Barata‐Vallejo, Al Postigo

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(12), P. 7756 - 7794

Published: May 25, 2023

A selection of perfluoroalkylation reactions aliphatic substrates that display methodological and synthetic amplitude will be studied, giving examples their applications mechanistic details. An array approaches for fluoroalkylation are documented; in particular, radical protocols prominent among methods. To effect, addition perfluoroalkyl radicals RF (RF=CnF2n+1, n > 1) to unsaturated organic serve as one the most direct efficacious ways access fluoroalkylated scaffolds. The syntheses perfluoroalkyl-substituted vinyl, alkynyl, allylic compounds; hydro-, iodo-, oxy-perfluoroalkylated alkanes olefins; carbonyl enamides, amides, thioamides, hydrazones; multicomponent studied. While there a number accomplished reports on organofluorination, we aim provide an overview radical-involved substrates, covering from 2018 early 2023, summarized Tables 1–4.

Language: Английский

Citations

41

Recyclable Cu@C3N4-Catalyzed Hydroxylation of Aryl Boronic Acids in Water under Visible Light: Synthesis of Phenols under Ambient Conditions and Room Temperature DOI
Mehwish Hussain Muhammad, Xiaolan Chen, Yan Liu

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2020, Volume and Issue: 8(7), P. 2682 - 2687

Published: Jan. 29, 2020

A heterogeneous photocatalyst based on copper-doped g-C3N4 was developed for the oxidative hydroxylation of aryl boronic acids into phenols at room temperature under irradiation blue light (460 nm). The reaction proceeded efficiently in water as a green solvent and air oxidant, giving various products with high yields short time. Importantly, this catalyst can be used least 5 times reactivities maintained.

Language: Английский

Citations

69

Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1‐a]iso‐quinolin‐6(5H)‐ones DOI
Kai Sun, Guofeng Li, Yuyang Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(10), P. 1947 - 1954

Published: Feb. 18, 2020

Abstract Here, a mild and general oxidative radical relay carbocyclization reaction with 2‐arylbenzoimidazoles cyclic ethers is reported. This method provides an efficient access to wide range of structurally diverse benzimidazo[2,1‐ ]isoquinoline‐6(5 H )‐ones under metal‐free conditions. The substrate scope, good functional group tolerance, scale‐up operation this are expected promote its potential applications in biotechnology pharmacy. magnified image

Language: Английский

Citations

68

Visible-light-induced photoredox-catalyzed synthesis of benzimidazo[2,1-a]iso-quinoline-6(5H)-ones DOI
Bin Wang,

Long Zou,

Lei Wang

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(3), P. 1229 - 1232

Published: Aug. 12, 2020

Language: Английский

Citations

65

Visible‐Light‐Induced Metal‐Free Synthesis of 2‐Phosphorylated Thioflavones in Water DOI

Xiao‐Ceng Liu,

Xiaolan Chen, Yan Liu

et al.

ChemSusChem, Journal Year: 2019, Volume and Issue: 13(2), P. 298 - 303

Published: Nov. 12, 2019

Abstract The introduction of phosphorus functional groups into the skeleton thioflavones is an attractive task and great significance. Herein, a metal‐free visible‐light‐induced radical cascade cyclization was developed for preparation 2‐phosphorylated from methylthiolated alkynones phosphine oxides. In water as green reaction medium, large number such were prepared, catalyzed by 4CzIPN [1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene] under visible‐light irradiation. These reactions could be performed at ambient temperature feature simple operation, wide scope, recyclability aqueous media.

Language: Английский

Citations

62