Computational and Experimental Studies on the α-Functionalization of Ketones Using Domino Reactions: A Strategy to Increase Chemoselectivity at the α-Carbon of Ketones

Molecules, Год журнала: 2025, Номер 30(5), С. 1114 - 1114

Опубликована: Фев. 28, 2025

A facile strategy to increase the chemoselectivity of domino reactions was proposed and successfully applied in α-functionalization ketones. The involved widening activation energy main reaction side through intermolecular interactions, thereby increasing reaction. In reaction, TMSCF3 acted as an excellent reagent which increased nucleophilicity DMF Van der Waals force reduced H2O a hydrogen bond. We found that can difference between using DFT calculations, greatly avoided formation by-products. recycled by rectification, average recovery rate 87.2%. XRD experiments, control experiments were performed support this mechanism. are confident has potential deliver significant practical advancements while simultaneously fostering broader innovation field synthesis.

Язык: Английский

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MeOH-Triggered Halogen-Atom Transfer of Unactivated Alkyl Bromides Enabling the Photoredox Giese Addition

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 18, 2025

Herein, a nickel-catalyzed, photoredox Giese addition reaction with readily accessible alkyl bromides, driven by available feedstock MeOH as the halogen-atom transfer (XAT) reagent, was successfully achieved under mild conditions. The versatility of this protocol demonstrated through range structurally varied bromides and Giese-type acceptors moderate to good yields. Mechanistic investigation highlights that formation radicals XAT tentatively prompted •CH2OH, which derived from sequential photo-oxidation/1,2-hydrogen-atom MeOH.

Язык: Английский

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Self-photocatalyzed three-component radical cascade reaction of quinoxalinones, simple alkenes and zhdankin reagent

Molecular Catalysis, Год журнала: 2024, Номер 557, С. 113981 - 113981

Опубликована: Март 1, 2024

Язык: Английский

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Photoinduced rapid Chloropropylation of Quinoxalin-2(1H)-ones with Cyclopropane and HCl

Molecular Catalysis, Год журнала: 2024, Номер 558, С. 114024 - 114024

Опубликована: Март 18, 2024

Язык: Английский

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Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(35), С. 7079 - 7084

Опубликована: Янв. 1, 2023

Polychloromethylative cyclization of N-alkenyl indoles was developed under metal-free conditions to afford tricyclic pyridoindolones and pyrroloindolones in moderate good yields. In the reaction, commercially available CHCl3 CH2Cl2 were employed as tri- dichloromethyl radical sources. Moreover, dichloromethylated polycyclic benzoimidazoles can also be obtained standard conditions.

Язык: Английский

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Polychloromethylation‐Initiated Radical 1,2‐Aryl Migration of α,α‐Diarylallyl Alcohols via Visible‐Light Photoredox Catalysis

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(31)

Опубликована: Июнь 15, 2023

Abstract A visible‐light induced radical 1,2‐aryl migration of α,α‐diarylallyl alcohols was developed under mild and metal‐free conditions. Commercially available CHCl 3 CH 2 Cl were used as tri‐ dichloromethyl precursors. Structurally diverse β‐polochloromethylated ketones obtained in good to moderate yields via neophyl‐type rearrangement. Besides, the polychloromethyl group can be easily transformed into other useful functional groups.

Язык: Английский

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Three‐Component Radical Cascade Reaction of Quinoxalinones, Alkenes and AgSCF₃

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(19), С. 3328 - 3334

Опубликована: Авг. 4, 2023

Abstract A convenient and practical protocol for the preparation of SCF 3 ‐containing quinoxalin‐2(1 H )‐one derivatives via K 2 S O 8 mediated difunctionalization alkenes with quinoxalinones AgSCF was developed. The preliminary study showed that a radical triggered cascade reaction process might be involved in current transformation.

Язык: Английский

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Decennary Update on Oxidative‐Rearrangement Involving 1,2‐Aryl C‐C Migration Around Alkenes: Synthetic and Mechanistic Insights

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

Опубликована: Май 14, 2024

In recent years, numerous methodologies on oxidative rearrangements of alkenes have been investigated, that produce multipurpose synthons and heterocyclic scaffolds potential applications. The present review focused recently established for transformation via 1,2-aryl migration in (2013-2023). Special emphasis has placed mechanistic pathways to understand the reactivity pattern different substrates, challenges enhance selectivity, key role reagents, effect substituents, how they affect rearrangement process. Moreover, synthetic limitations future direction also discussed. We believe, this offers new insight develop elegant precursors approaches explore utilization alkene-based compounds natural product synthesis functional materials.

Язык: Английский

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Recent Advances in Strategies for Halide Atom Transfer (XAT) and Their Applications

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(6), С. 1733 - 1733

Опубликована: Янв. 1, 2024

Язык: Английский

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Light-fuelled nitro-reduction via cascaded electron donor-acceptor complexes in aqueous media

Green Chemistry, Год журнала: 2024, Номер 26(18), С. 9682 - 9689

Опубликована: Янв. 1, 2024

Developed herein is a metal-free method for nitro reduction via cascade electron donor acceptor complex photoexcitation in aqueous media.

Язык: Английский

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