Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 110112 - 110112

Опубликована: Июнь 25, 2024

Язык: Английский

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Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6117 - 6125

Опубликована: Апрель 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Язык: Английский

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Electrochemical Synthesis of 2-Amino-1,3-benzoxazines via TBAI-mediated Desulfurative Cyclization of Isothiocyanates and 2-Aminobenzyl Alcohols

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 5, 2025

An efficient one-step protocol has been developed to access a variety of 2-amino-1,3-benzoxazine derivatives via tetrabutylammonium iodide-mediated electrochemical desulfurative cyclization isothiocyanates and 2-aminobenzyl alcohols. The reaction proceeds through cycle involving in situ iodine generation, cyclization, iodide regeneration, efficiently forming intermolecular C–O C–N bonds affording 2-amino-1,3-benzoxazines moderate excellent yields. practical utility this strategy is evidenced by its broad substrate scope, good functional group compatibility, scalability gram-scale synthesis, metal- oxidant-free conditions.

Язык: Английский

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Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1679 - 1685

Опубликована: Март 15, 2024

Comprehensive Summary A novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 + OTf − ) for trifluoromethylation imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis TT–CF without requirement external oxidants or catalysts, aligning with principles green chemistry. wide range including imidazo[1,2‐ a ]pyridines benzo[ d ]imidazo[2,1‐ b ]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility various functional groups broad substrate scope. Moreover, method's applicability one‐pot sequential reactions enables reduction waste resource consumption by eliminating need intermediate purification steps.

Язык: Английский

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Redox Reactions of Organic Molecules Using Rotating Magnetic Field and Metal Rods

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(26), С. 18143 - 18150

Опубликована: Июнь 25, 2024

In recent years, redox reactions have harnessed light or mechanical energy to enable the formation of chemical bonds. We postulated a complementary approach that electromagnetic induction could promote reaction organic molecules using rotating magnetic field and metal rods. Here, we report electromotive force activates redox-active trifluoromethylating reagents. This magnetoredox system can be applied trifluoromethylation heteroarenes with high regioselectivity hydrotrifluoromethylation alkenes without need for catalysts additives.

Язык: Английский

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Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8821 - 8826

Опубликована: Окт. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Язык: Английский

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Visible-Light Photoredox-Catalyzed Difunctionalization of Alkynes with Quinoxalin-2(1H)-Ones, P₄S₁₀, and Alcohols

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10974 - 10986

Опубликована: Июль 24, 2024

Visible-light photoredox-catalyzed method has been developed for the synthesis of quinoxalin-2(1H)-one-containing vinyl phosphorodithioates via direct difunctionalization alkynes with quinoxalin-2(1H)-ones, P4S10 and alcohols. This four-component reaction could be carried out under metal-free mild conditions, affording a number in moderate to good yields Z-isomers as major products. Photocatalytic radical mechanism is proposed based on results trapping fluorescence quenching experiments.

Язык: Английский

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Photocatalytic synthesis of polyfluoroalkylated dihydropyrazoles and tetrahydropyridazines

Chemical Communications, Год журнала: 2024, Номер 60(77), С. 10764 - 10767

Опубликована: Янв. 1, 2024

A photocatalytic trifluoromethylation/cyclization reaction of

Язык: Английский

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Electrochemical umpolung of C‐H nucleophiles bearing three electron‐withdrawing groups to trigger radical 1,2‐alkylarylations of allylic alcohols

Advanced Synthesis & Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Янв. 31, 2025

Abstract The electrochemical catalyst‐free generation of carbon radicals bearing three electron‐withdrawing groups from the corresponding C−H nucleophiles remains unexplored. To this end, we report a direct electro‐oxidation strategy to access these electrophilic under conditions. Enabled by strategy, radical 1,2‐alkylarylations allylic alcohols was realized, affording β ‐quaternary ketones with high functional group compatibility. This protocol is operationally simple and also easy scale up.

Язык: Английский

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g-C₃N₄-Based Heterogeneous Photocatalyzed Synthesis and Evaluation of Antitumor Activities of Fluoroalkylated 4H-Pyrido[1,2-a]pyrimidin-4-ones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 26, 2025

The first example of heterogeneous photoredox-catalyzed fluoroalkylation 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed. With low-cost commercial g-C3N4 as the recyclable photocatalyst and cheap sodium fluoroalkyl sulfonates source, a variety fluoroalkylated pyridopyrimidinones were constructed in moderate to high yields. present reaction can be easily scaled up with good efficiency, catalytic system reused 5 times slight loss activities. Furthermore, biological activity synthesized compounds was preliminarily investigated.

Язык: Английский

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