Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

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

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Fluorination and fluoroalkylation of alkenes/alkynes to construct fluoro-containing heterocycles

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

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Recyclable Perovskite as Heterogeneous Photocatalyst for Aminomethylation of Imidazo‐Fused Heterocycles

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

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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

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

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

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

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Radical Perfluoroalkylation of Aliphatic Substrates

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

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Recyclable Cu@C₃N₄-Catalyzed Hydroxylation of Aryl Boronic Acids in Water under Visible Light: Synthesis of Phenols under Ambient Conditions and Room Temperature

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

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

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

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

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

Published: Aug. 12, 2020

Language: Английский

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

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

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