Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2830 - 2848

Опубликована: Янв. 1, 2023

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights synthetic applications have been summarized.

Язык: Английский

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Organoelectrophotocatalytic C–H Silylation of Heteroarenes

Organic Letters, Год журнала: 2023, Номер 25(6), С. 1008 - 1013

Опубликована: Фев. 3, 2023

An organoelectrophotocatalytic approach for the C-H silylation of heteroarenes through dehydrogenation cross-coupling with H2 evolution has been developed. The strategy is carried out under a simple and efficient monocatalytic system by employing 9,10-phenanthrenequinone both as an organocatalyst hydrogen atom transfer (HAT) reagent, which avoids need external HAT oxidant, or metal reagent. A variety can be compatible in satisfactory yields excellent regioselectivity.

Язык: Английский

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Electrophilic Halospirocyclization of N-Benzylacrylamides to Access 4-Halomethyl-2-azaspiro[4.5]decanes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13610 - 13621

Опубликована: Сен. 11, 2023

An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize wide variety 4-halomethyl-2-azaspiro[4.5]decanes satisfactory yields. The approach further highlighted through gram-scale synthesis diverse transformations spiro products.

Язык: Английский

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A Traceless Heterocyclic Amine Mediator in Regioselectivity−Switchable Formal [1 + 2 + 2] Cycloaddition Reaction to 1,3,4- and 1,4,5-Trisubstituted Pyrazoles

Organic Letters, Год журнала: 2023, Номер 25(3), С. 512 - 516

Опубликована: Янв. 12, 2023

Switchable multicomponent reactions have been attractive tools for the construction of compound libraries with skeleton diversity and complexity by slightly changing reaction conditions. Described herein is a regioselectivity-switchable formal [1 + 2 2] cycloaddition from difluoroalkyl compounds, enaminones, RNHNH2, ultimately using 1-methylindazol-3-amine as traceless mediator to switch inherent regioselectivity 1,3,4-trisubstituted pyrazole formation 1,4,5-trisubstituted pyrazoles. Remarkable features this work include mild conditions, simple operation, broad scopes.

Язык: Английский

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Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

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Organophotoelectrochemical silylation cyclization for the synthesis of silylated 3-CF₃-2-oxindoles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3585 - 3590

Опубликована: Янв. 1, 2023

An organophotoelectrochemical approach for silylation cyclization of CF3-substituted N -arylacrylamides with organosilanes under transition-metal-free and oxidant-free conditions has been developed.

Язык: Английский

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Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1H)-ones via polysulfide anion photocatalysis

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(8), С. 1708 - 1713

Опубликована: Янв. 1, 2024

A visible-light-induced radical relay cyclization/C-C bond formation of quinoxalin-2(1

Язык: Английский

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Seminormal-BrCH₂CH₂OH-mediated electrochemical epoxidation of unactivated olefins

Green Chemistry, Год журнала: 2024, Номер 26(4), С. 2157 - 2161

Опубликована: Янв. 1, 2024

An electrochemical epoxidation of unactivated olefins with water as the source oxygen has been developed.

Язык: Английский

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Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions

Organic Letters, Год журнала: 2023, Номер 25(18), С. 3314 - 3318

Опубликована: Май 1, 2023

We disclose herein an efficient photochemical formal [3+2+1] annulation strategy for the transformation of diazocarbonyl compounds into various fluorinated nitrogen-containing heterocycles. This is characterized by reacting fluoroalkyl radicals with α-diazoketones, which are used as infrequent denitrogenated synthons under visible light. Moreover, a wide range N-heterocycles containing precious CF3 and perfluoroalkylated groups constructed in moderate to good yields. Notably, this may provide fruitful path synthesis complex organofluorides via diazo/fluorine/radical chemistry.

Язык: Английский

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Chloride‐Promoted Photoelectrochemical C—H Silylation of Heteroarenes^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(22), С. 2963 - 2968

Опубликована: Июнь 24, 2023

Comprehensive Summary A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H 2 evolution has been developed. The depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated light‐induced homolytic cleavage Cl , in which was produced by electrochemical oxidation chloride. large number silylated heterocyclic molecules are rapidly constructed satisfactory yields without relying oxidants and metal reagents.

Язык: Английский

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