Visible Light Induced Photocatalyst‐Free C−X (X=B, C, O, P,S, Se) Bond Formation of Aryl Halides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1719 - 1737

Published: Feb. 29, 2024

Abstract Aryl halides are one of the most important chemical feedstocks in pharmaceuticals due to its easy accessibility, inexpensiveness, and widely utilized as aryl radical precursors organic synthetic chemistry. Conventionally, stoichiometric reagents such AIBN/n‐Bu 3 SnH were used for generation from halides, suffered requirement toxic initiators, high temperature thus, development simple, mild strategies highly desirable. Recently, visible light mediated received considerable attention, allowing under reaction conditions. The present review described recent breakthroughs advancements photocatalyst‐free C−B/C/O/P/Se/S bond formation halides.

Language: Английский

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Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 636 - 641

Published: Jan. 10, 2024

A photochemical halogen-bonding-assisted synthesis of vinyl sulfones via radical–radical cross-coupling bromines and sodium sulfinates is developed. This methodology offers a facile efficient approach to various with excellent functional group tolerance under metal-, photocatalyst-, base-, oxidant-free conditions. The reaction also applicable for the late-stage functionalization drug molecules hectogram scale. Moreover, instead sulfites being prepared, these reactions could be conducted using sulfonyl chlorides in one-pot method.

Language: Английский

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Iodoarene-directed photoredox β-C(sp³)–H arylation of 1-(o-iodoaryl)alkan-1-ones with cyanoarenes via halogen atom transfer and hydrogen atom transfer

Chemical Science, Journal Year: 2024, Volume and Issue: 15(17), P. 6522 - 6529

Published: Jan. 1, 2024

Site selective functionalization of inert remote C(sp

Language: Английский

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CO₂^•– Enabled Synthesis of Phenanthridinones, Oxindoles, Isoindolinones, and Spirolactams

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

We report herein that photoinduced CO2•– enabled reductive intramolecular radical cyclization of a variety aryl iodide derivatives to the corresponding phenanthridinone, oxindole, isoindolinone, and spirolactam in good yields. Preliminary mechanistic studies suggested generation through homolysis cesium formate presence light, further involvement was directly proved by trapping with diphenyl styrene TEMPO.

Language: Английский

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Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.

Language: Английский

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Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

A photoinduced and catalyst-free radical cyclization process for the synthesis of 3,3-disubstituted oxindoles is reported. This method utilizes readily available α-bromoanilides as substrates, showcasing a broad substrate scope. The reaction mechanism facilitated by photoactivated charge transfer complex based on halogen bonding α-bromoanilide with TMG alcohol.

Language: Английский

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Synthesis of 3-sulfonylisoindolin-1-ones from olefinic amides and sodium sulfinates via electrooxidative tandem cyclization

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5897 - 5901

Published: Jan. 1, 2024

Sulfonyl groups are motifs that widely found in biologically active compounds and drug molecules, many isolated natural products as well pharmaceuticals contain sulfonyl groups. Herein, we present the synthesis of sulfonyl-substituted isoindolones by a electrochemical oxidative radical cascade cycloaddition reaction olefinic amides with sodium sulfite under oxidant- catalyst-free conditions. Various sulfinates were compatible gave desired yields up to 99%.

Language: Английский

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Electron donor–acceptor complex enabled cascade reaction of unprotectedo-anilide aryl chlorides for heterocycle synthesis

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1219 - 1223

Published: Jan. 1, 2023

An electron donor–acceptor complex strategy that enabled photoactivation of aryl chlorides has been reported with the toluene anion or t BuOK as donor.

Language: Английский

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