The diacetyliminoxyl radical in oxidative functionalization of alkenes

Budnikov, Alexander S.; Krylov, Igor B.; Lastovko, Andrey V.; Dolotov, Roman A.; Shevchenko, Mikhail I.; Terent'ev, Alexander O.

doi:10.1039/d3ob00925d

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00925d

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The diacetyliminoxyl radical in oxidative functionalization of alkenes

Alexander S. Budnikov,

Igor B. Krylov,

Andrey V. Lastovko

et al.

Abstract: The intermolecular oxime radical addition to C=C bond was observed and studied for the first time. Diacetyliminoxyl radical was proposed as a novel reagent for the functionalization of unsaturated substrates...

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Cited by 1 publication

References 99 publications

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

Budnikov,

Krylov,

Shevchenko

et al. 2023

Molecules

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

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

Budnikov,

Krylov,

Shevchenko

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

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The diacetyliminoxyl radical in oxidative functionalization of alkenes

Abstract: The intermolecular oxime radical addition to C=C bond was observed and studied for the first time. Diacetyliminoxyl radical was proposed as a novel reagent for the functionalization of unsaturated substrates...

Cited by 1 publication

References 99 publications

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

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

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