One-Pot Transformation of Aldehydes to Ketones via Minisci-Type Reaction of Imines

Organic Letters, Год журнала: 2023, Номер 25(48), С. 8751 - 8755

Опубликована: Ноя. 28, 2023

A method for the conversion of aldehydes to ketones via preliminary formation aldiminines is described. The imines are involved in acid promoted Minisci-type reaction with alkyl radicals generated from esters N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after addition iminium ions believed be key intermediates, which determine outcome.

Язык: Английский

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Zinc Chelate Complexes of N‐Acyl Hydrazones as Substrates for Addition of Alkyl and Fluorinated Radicals

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(15), С. 2636 - 2642

Опубликована: Июль 13, 2023

Abstract Zinc chelate complexes can be generated in situ from N‐acyl hydrazones by treatment with isopropyl zinc iodide. These couple alkyl and fluorinated radicals under photoredox conditions. Alkyl were organozinc halides using an organic photocatalyst afford hydrazines as a result of reductive mode addition. Fluorinated formed perfluorinated iodides conditions leading to fluoroalkylated via neutral reaction pathway.

Язык: Английский

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Current trends in organic chemistry: contribution of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Russian Chemical Bulletin, Год журнала: 2024, Номер 73(9), С. 2423 - 2532

Опубликована: Сен. 1, 2024

Язык: Английский

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Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Дек. 17, 2024

Abstract Azomethines is a class of compounds, which have traditionally served as electrophilic substrates, but their reactions with radicals long been limited. Photocatalysis provided ample opportunities for promoting these reactions, wide variety reagents serving precursors radicals. Besides regular addition mode at the azomethine fragment, oxidative pathway, in C=N bond remains product, has become possible by proper selection redox catalyst. This review summarizes new developments this rapidly developing field over past five years. New concepts on activation towards radical attack are discussed.

Язык: Английский

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C–O Coupling of Hydrazones with Diacetyliminoxyl Radical Leading to Azo Oxime Ethers—Novel Antifungal Agents

Molecules, Год журнала: 2023, Номер 28(23), С. 7863 - 7863

Опубликована: Ноя. 30, 2023

Selective oxidative C-O coupling of hydrazones with diacetyliminoxyl is demonstrated, in which plays a dual role. It an oxidant (hydrogen atom acceptor) and O-partner for the coupling. The reaction completed within 15-30 min at room temperature, compatible broad scope hydrazones, provides high yields most cases, requires no additives, makes it robust practical. proposed leads to novel structural family azo compounds, oxime ethers, were discovered be highly potent fungicides against spectrum phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, moniliforme, Bipolaris sorokiniana, Sclerotinia sclerotiorum).

Язык: Английский

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Photoredox catalyzed release of carbon-based radicals from 2-substituted-1,3-imidazolidines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 661 - 667

Опубликована: Дек. 7, 2023

We describe herein easily oxidizable 2-substituted-1,3-imidazolidines for the photocatalyzed generation of (substituted) alkyl radicals forging C(sp 3 )–C(sp ) bonds under metal-free conditions.

Язык: Английский

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