Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent

Green Chemistry, Год журнала: 2022, Номер 24(4), С. 1732 - 1737

Опубликована: Янв. 1, 2022

A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocyclesunder air and room temperature conditions.

Язык: Английский

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Photoredox catalysis harvesting multiple photon or electrochemical energies

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 1055 - 1145

Опубликована: Июль 28, 2023

Photoredox catalysis (PRC) is a cutting-edge frontier for single electron-transfer (SET) reactions, enabling the generation of reactive intermediates both oxidative and reductive processes via photon activation catalyst. Although this represents significant step towards chemoselective and, more generally, sustainable chemistry, its efficacy limited by energy visible light photons. Nowadays, excellent alternative conditions are available to overcome these limitations, harvesting two different but correlated concepts: use multi-photon such as consecutive photoinduced electron transfer (conPET) combination photo- electrochemistry in synthetic photoelectrochemistry (PEC). Herein, we review most recent contributions fields activations organic functional groups. New opportunities chemists captured, selective reactions employing super-oxidants super-reductants engage unactivated chemical feedstocks, scalability up gram scales continuous flow. This provides comparisons between techniques (multi-photon photoredox PEC) help reader fully understand their similarities, differences potential applications therefore choose which method appropriate given reaction, scale purpose project.

Язык: Английский

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Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2777 - 2781

Опубликована: Фев. 5, 2024

2,1,3-Benzothiadiazole is widely used as a privileged scaffold in pharmaceuticals and organic functional materials. Nonetheless, many current methods for the functionalization of 2,1,3-benzothiadiazole rely on preactivation, transition metal catalysts/promoters, or an elevated reaction temperature. Herein we disclose transition-metal-free visible-light-induced photocatalytic method direct C–H alkylation using readily accessible carboxylic acid derivatives, i.e., N-hydroxyphthalimide esters (NHPEs), alkylating reagents under room This mild scalable highlighted by late-stage installation benzothiadiazole drugs natural products.

Язык: Английский

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Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

Chemical Communications, Год журнала: 2021, Номер 57(73), С. 9276 - 9279

Опубликована: Янв. 1, 2021

A simple and efficient iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1- a ]isoquinolin-6(5 H )-ones indolin-2-ones has been developed.

Язык: Английский

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Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones

Journal of Catalysis, Год журнала: 2022, Номер 417, С. 473 - 480

Опубликована: Дек. 30, 2022

Язык: Английский

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Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Язык: Английский

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Recent advances in the photocatalytic synthesis of aldehydes

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 4198 - 4210

Опубликована: Янв. 1, 2023

This review summarizes the recently developed photocatalytic strategies for installation of formyl group into various scaffolds.

Язык: Английский

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Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

Organic Letters, Год журнала: 2021, Номер 24(1), С. 349 - 353

Опубликована: Дек. 14, 2021

Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation dihydroquinolinones. In this protocol, sustainable visible light was used as energy source, organic light-emitting molecule 4CzIPN served efficient photocatalyst. This reaction system features exclusive 6-endo-trig selectivity with generally good yield range functionalized dihydroquinolinones dihydrobenzoquinolinones. Mechanistical studies reveal feasibility both 1,3-H shift intersystem crossing diradical intermediate.

Язык: Английский

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

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(12), С. 2080 - 2085

Опубликована: Май 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

Язык: Английский

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Metal-free synthesis of sulfonylated indolo[2,1-a]isoquinolines from sulfur dioxide

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(13), С. 3521 - 3526

Опубликована: Янв. 1, 2022

Access to sulfonylated indolo[2,1- a ]isoquinolines through an efficient three-component reaction of 2-aryl- N -acryloyl indoles, sulfur dioxide and aryldiazonium tetrafluoroborates is developed.

Язык: Английский

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