Generation and Application of Aryl Radicals Under Photoinduced Conditions

Chemistry - A European Journal, Год журнала: 2024, Номер 30(31)

Опубликована: Март 28, 2024

Abstract Photoinduced aryl radical generation is a powerful strategy in organic synthesis that facilitates the formation of diverse carbon‐carbon and carbon‐heteroatom bonds. The synthetic applications photoinduced complex compounds, including natural products, physiologically significant molecules, functional materials, have received immense attention. An overview current developments production methods their uses given this article. A generalized idea how to choose reagents approach for radicals described, along with techniques associated mechanistic insights. Overall, article offers critical assessment results as well selection reaction parameters specific context cascades, cross‐coupling reactions, functionalization, selective C−H functionalization substrates.

Язык: Английский

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Sustainable Synthesis through Catalyst‐Free Photoinduced Cascaded Bond Formation

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(14)

Опубликована: Май 8, 2024

The beginning of photochemical reactions revolutionized synthetic chemistry through sustainable practices. This review explores cutting-edge developments in leveraging light-induced processes for generating cascaded C-C and C-hetero bonds without catalysts. Significantly, catalyst-free photoinduced methodologies have garnered considerable attention, especially the creation varied heterocyclic frameworks drug design synthesis natural products. article delves into underlying mechanisms, addresses limitations, evaluates various methodologies, emphasizing potential photocatalyst transition metal-free to enhance sustainability. Divided two sections, it covers recent strides C-heteroatom multiple bond formation reactions.

Язык: Английский

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Mn(OAc)3 promoted radical cyclization of vinyl isocyanides: Synthesis of isoquinoline-1-sulfonates and derivatives

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155629 - 155629

Опубликована: Май 1, 2025

Язык: Английский

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Recent Advances in Photoinduced Radical Cascade Cyclizations Enabling Five-Membered N-Heterocycle Formation

Topics in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Photoactivation of Thianthrenium Salts: An Electron-Donor–Acceptor (EDA)-Complex Approach

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

Опубликована: Май 14, 2025

Thianthrenium salts have emerged as one of the most versatile reagents, gaining significant popularity within synthetic community for their utility in construction C-C and C-X (X = N, O, S, P, halogens) bonds. The use photoredox transition metal catalysis with thianthrenium C-heteroatom bond formation is well established. However, these methods require elevated temperatures, expensive catalysts, ligands under stringent conditions effective execution. In contrast, photocatalysis- transition-metal-free approaches constructing bonds using salt derivatives become increasingly sought after. this regard, electron-donor-acceptor (EDA)-complex reactions a powerful strategy organic synthesis, eliminating need photocatalysts visible light irradiation. EDA-complex photochemistry exploits electron-acceptor properties salts, facilitating rapid generation radical intermediates via C-S cleavage. These play pivotal role enabling variety valuable formations. Perspective, we highlight advances EDA-complex-mediated involving mechanisms, substrate scope, limitations For sake brevity, article organized into five main sections: (1) Nitrogen-based donor reactions, (2) Oxygen-based (3) Sulfur-based (4) Phosphorus-based (5) π-based focus on C-C, C-S, C-B C-P

Язык: Английский

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Mn(OAc)₃-Promoted Sulfonation–ipso-Cyclization Cascade via the SO₃^– Radical: The Synthesis of Spirocyclic Sulfonates

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 14140 - 14155

Опубликована: Сен. 18, 2023

A radical sulfonation–ipso-cyclization cascade promoted by Mn(OAc)3·2H2O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) is reported. total of 30 spirocyclic sulfonates were synthesized under mild conditions. We also demonstrate a modular synthesis approach in multiple steps for the preparation various azaspiro[4,5]-trienone-based sulfonamides sulfonate esters.

Язык: Английский

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Visible-light-induced construction of 2-aryl or 2-alkyl benzothiazoles via radical addition cascade cyclization of 2-isocyanoaryl thioethers

Tetrahedron Letters, Год журнала: 2023, Номер 129, С. 154757 - 154757

Опубликована: Сен. 17, 2023

Язык: Английский

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Visible Light Catalyzed Stannylation of Aryl Halides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1899 - 1903

Опубликована: Март 1, 2024

Abstract A visible light‐mediated strategy for the preparation of aromatic stannanes from aryl halides (mostly bromides) is presented herein. The reaction proceeds under metal‐ and additive‐free conditions exhibits a broad substrate scope. products obtained have been employed in C−C bond formation via Stille cross‐coupling reactions. Mechanistic investigation evidenced key role both radical trimethylstannyl Ar−Sn formation.

Язык: Английский

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Accessing 2‐(chalcogen)benzothiazoles via electrochemically mediated intermolecular cyclization of isocyanides with thiols or diselenides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Авг. 22, 2024

Abstract 2‐(chalcogen)benzothiazoles are frequently used as core structures for the development of pharmaceutical agents. A strategy synthesis under electrooxidative conditions using isocyanides, thiols or diselenides substrates was developed. This protocol allows access to structurally diverse in good yields and with functional group tolerance, which does not require heavy metal catalysts exogenous oxidants. Furthermore, gram‐scale performed demonstrate scale‐up applicability this reaction.

Язык: Английский

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Visible Light‐Induced Radical Tandem Cyclization of o‐Isocyanodiaryl Amines with Arylthiodifluoroalkyl 2‐Pyridyl Sulfones or Difluormethyl‐ Bromides

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(41)

Опубликована: Авг. 6, 2024

Abstract A visible‐light‐induced photoredox‐catalyzed radical tandem cyclization of o ‐isocyanodiaryl amines with arylthiodifluoroalkyl 2‐pyridyl sulfones or difluormethyl bromides has been realized for the first time. The reaction works a broad range substrates and provides simple efficient method synthesis 11‐difluoromethyl‐substituted dibenzodiazepines from easily available starting materials in very mild conditions.

Язык: Английский

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