Radical-Polar Crossover Enabled Triple Cleavage of CF₂Br₂: A Multicomponent Tandem Cyclization to 3-Fluoropyrazoles

Organic Letters, Год журнала: 2023, Номер 25(32), С. 6062 - 6066

Опубликована: Авг. 8, 2023

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation reactive intermediate gem-difluorovinylimine ion key this transformation. This protocol unlocks reactivity adds significant synthetic values fluorine chemistry.

Язык: Английский

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Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Год журнала: 2023, Номер 35(2), С. 108977 - 108977

Опубликована: Авг. 26, 2023

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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Oxygen Migration–Defluorination Strategy Enables the Aminocarbonylation of Enaminones with o-Aminobenzamides and CF₂Br₂

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 24, 2025

The development of different concept approaches and user-friendly carbonyl surrogates for aminocarbonylation is highly desirable. Herein, we report the photocatalytic enaminones with easily available o-aminobenzamides CF2Br2 through an oxygen migration-defluorination strategy. reaction features switchable transformation construction carbamoyl-substituted enol products allows expedient synthesis fully substituted maleimides under mild conditions.

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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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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Harnessing the power of polyol-based polyesters for biomedical innovations: synthesis, properties, and biodegradation

Journal of Materials Chemistry B, Год журнала: 2023, Номер 11(40), С. 9597 - 9629

Опубликована: Янв. 1, 2023

Polyesters based on polyols have emerged as promising biomaterials for various biomedical applications, such tissue engineering and drug delivery systems, due to their biocompatibility, biodegradability, versatile physicochemical properties.

Язык: Английский

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“Alkene-to-Alkene” Difunctionalization of Enaminones for the Synthesis of Polyfunctionalized Alkenes by Transition-Metal-Free C–H and C–N Bond Transformation

Organic Letters, Год журнала: 2023, Номер 25(47), С. 8451 - 8456

Опубликована: Ноя. 16, 2023

The three-component reactions of enaminones, disulfides, and alcohols for the synthesis polyfunctionalized alkenes have been realized via C-H C-N bond transformation on enaminones. proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. application alkene products divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, isoxazoles, simple annulation has also verified.

Язык: Английский

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Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 109683 - 109683

Опубликована: Март 2, 2024

Язык: Английский

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Язык: Английский

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