Photochemical dearomative skeletal modifications of heteroaromatics

Chemical Society Reviews, Год журнала: 2024, Номер 53(12), С. 6600 - 6624

Опубликована: Янв. 1, 2024

Dearomatization has emerged as a powerful tool for rapid construction of 3D molecular architectures from simple, abundant, and planar (hetero)arenes. The field evolved beyond simple dearomatization driven by new synthetic technology development. With the renaissance photocatalysis expansion activation mode, last few years have witnessed impressive developments in innovative photochemical methodologies, enabling skeletal modifications dearomatized structures. They offer truly efficient useful tools facile highly complex structures, which are viable natural product synthesis drug discovery. In this review, we aim to provide mechanistically insightful overview on these innovations based degree alteration, categorized into dearomative functionalization editing, highlight their utilities.

Язык: Английский

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Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(22)

Опубликована: Апрель 16, 2024

Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.

Язык: Английский

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Photoredox/NHC cooperative catalysis for alkylacylation of styrenes: An alternative method for the synthesis of γ-aminoketones

Tetrahedron Letters, Год журнала: 2025, Номер 156, С. 155450 - 155450

Опубликована: Янв. 8, 2025

Язык: Английский

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Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO₂

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4194 - 4199

Опубликована: Май 15, 2024

A photoredox-catalyzed sequential α-formyl/carboxylation of alkenes with glyoxylic acid acetals and CO

Язык: Английский

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Advances in photochemical/electrochemical synthesis of heterocyclic compounds from carbon dioxide

Green Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This paper reviews progress in the photochemical/electrochemical construction of heterocyclic compounds using CO 2 , differentiating between various reaction types and elucidating their underlying mechanisms as well potential applications.

Язык: Английский

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Visible-Light-Promoted Cascade Carboxylation/Arylation of Unactivated Alkenes with CO₂ for the Synthesis of Carboxylated Indole-Fused Heterocycles

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6341 - 6346

Опубликована: Июль 18, 2024

Described here is a visible-light-promoted cascade carboxylation/arylation of indole-tethered unactivated alkenes with CO

Язык: Английский

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Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155468 - 155468

Опубликована: Янв. 1, 2025

Язык: Английский

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Copper-PMHS System-Enabled Reductive Cyclization of o-Aminobenzamides with CO₂ as a Single-Carbon Synthon

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 18, 2025

Chemical utilization of carbon dioxide (CO2) has emerged as a sustainable access for synthesizing high-value chemicals. Continuously designing the more practical reaction systems is large importance. Herein, an unprecedented and powerful copper-PMHS reductive system o-aminobenzamides with CO2 disclosed. Synthetically, diverse range quinazolinones (>70 examples) are rapidly assembled excellent functional group tolerance in good yields. Moreover, building other types heterocycles such benzothiazoles benzimidazoles also allowable. Mechanistically, differing from reported carbonylation cases, this finding represents scarce example single-carbon atom synthon PMHS system.

Язык: Английский

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Dearomatization of Aromatic Compounds: A Decade Review

Asian Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

Abstract Dearomatization offers an efficient strategy for directly converting arenes into cyclic molecules. In this review, we discuss representative examples of dearomatization reactions through five modes: (1) radical dearomatization, (2) halofunctionalization‐dearomatization, in which three‐membered intermediates were frequently involved, (3) nucleophilic mainly about electron‐rich arenes, (4) oxidative and (5) reductive dearomatization. Compared to heteroarenes, simple benzene are more challenging participate reactions. recent years, fewer reports have focused on benzene. Heteroarenes, inherently or easily activated, tend undergo readily. This review highlights a decade progress including indoles, benzofurans, benzothiophenes, thiophenes, furans, naphthols, naphthalenes, quinolines, pyridines, nitrobenzenes, benzenes. It also analyzes their mechanisms strategies. We hope will aid future research field.

Язык: Английский

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Advances in the Synthesis of Carboxylic Acid by Photochemical Conversion of CO2

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(10), С. 2997 - 2997

Опубликована: Янв. 1, 2024

Язык: Английский

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