Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2H-Chromenes

Organic Letters, Год журнала: 2022, Номер 24(31), С. 5791 - 5796

Опубликована: Авг. 2, 2022

A novel visible-light-mediated difluoroalkylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-arylvinyl)-2-(vinyloxy)benzenes for the synthesis bis-difluoroalkylated benzoxepines 2H-chromenes is developed. This method features mild reaction conditions, good regioselectivity, a wide substrate scope, functional-group compatibility, late-stage modification. Preliminary mechanistic studies reveal that generation CF2CO2Et radical more prone to with double bond aryl group.

Язык: Английский

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Photoinduced Construction of Thieno[3,4-c]quinolin-4(5H)-ones/Selenopheno[3,4-c]quinolin-4(5H)-ones Using Diphenyl Disulfide or Diphenyl Diselenide as Sulfur or Selenium Sources

The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(2), С. 828 - 837

Опубликована: Дек. 28, 2022

A photocatalytic synthesis of thieno[3,4-c]quinolin-4(5H)-ones/selenopheno[3,4-c]quinolin-4(5H)-ones using diphenyl disulfide or diselenide as sulfur selenium sources was developed. Two C-S/Se bonds and one C-C bond were constructed simultaneously without transition metals other additives.

Язык: Английский

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Electrosynthesis of bridged or fused sulfonamides through complex radical cascade reactions: divergence in medium-sized ring formation

Chemical Science, Год журнала: 2023, Номер 14(13), С. 3541 - 3547

Опубликована: Янв. 1, 2023

Radical cascade addition is one of the most important and efficient strategies for synthesis valuable heterocycles with structural diversity complexity.

Язык: Английский

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Visible-Light-Initiated Catalyst-Free Radical Annulation Reactions of 1,6-Enynes and Aryl Sulfonyl Bromide to Assemble Sulfonation/Bromination Succinimide Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3857 - 3867

Опубликована: Фев. 22, 2024

In the present study, environment-friendly visible-light-promoted strategy is used to perform an efficient, simple, and straightforward photocatalytic succinimide derivative synthesis from reaction of 1,6-enynes aryl sulfonyl bromide at room temperature under air ambient conditions. This method features mild conditions, broad substrate scope, high yields, excellent configurational selectivity. addition, all atoms substrates involved in converge product structures, showing a atomic economy. Moreover, most important characteristic this study that no photocatalyst additives are used, while key factor triggers visible light, indicating has practical value.

Язык: Английский

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Mn‐Mediated Radical Cascade Cyclization of 1,6‐Enynes with Arylboronic Acids to Access Dihydrobenzo[b]fluorenones

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(24), С. 4409 - 4414

Опубликована: Дек. 1, 2022

Abstract Herein, we report the synthesis of functionalized dihydro‐benzo[ b ]fluorenones through a manganese‐mediated cascade radical cyclization β ‐alkynyl propenones [1,6‐enynes] with arylboronic acids. In present strategy, in‐situ generated aryl undergoes chemo‐selective addition followed by 5‐ exo‐trig cyclization. The reaction is emphasized high atom‐ and step‐economy construction three new C−C bonds to access dihydrobenzo[ in 68–81% yield under mild conditions. synthetic efficacy developed method evidenced C−N bonds. magnified image

Язык: Английский

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Copper(I)-Catalyzed Radical Carbamylation/Cyclization of 2-Aryl-N-methacryloylindoles with Substituted Formamides to Assemble Amidated Indolo[2,1-a]isoquinolin-6(5H)-ones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16352 - 16364

Опубликована: Ноя. 16, 2023

An efficient synthesis of amidated indolo[2,1-a]isoquinolin-6(5H)-ones has been achieved via copper(I)-catalyzed radical carbamylation/cyclization 2-aryl-N-methacryloylindoles with substituted formamides. In this reaction, an isoquinoline ring was constructed by carbamylation a carbon-carbon double bond in 2-arylindoles. This strategy successfully introduces the amide group into indolo[2,1-a]isoquinoline skeleton and advantages such as wide substituent scope, mild reaction conditions, high regioselectivity, good to excellent yields.

Язык: Английский

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Substituent-Controlled Copper-Catalyzed Trifluoromethylation of 1,7-Dienes: Synthesis of Mono- and Bis-trifluoromethylated Benzoxepines

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7261 - 7266

Опубликована: Авг. 21, 2024

A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents double bond allyl group in 1,7-dienes. large-scale operation late-stage functionalization bioactive molecules reveal promising utility this protocol.

Язык: Английский

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Radical-Mediated Tandem Cyclization to Construct Seven-Membered Nitrogen/Oxygen Heterocycles

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(12), С. 3995 - 3995

Опубликована: Янв. 1, 2022

Owing to the special chemical structure of seven-membered heterocyclic skeleton and unique properties heteroatoms contained, it is widely used in natural products drug molecules.However, development synthetic methodology for these structures challenging due thermodynamic kinetic characteristics nitrogen/oxygen-containing frameworks, as well their own cross-ring forces.Therefore, great significance develop simple efficient methods construction compounds.Compared with traditional methods, radical reactions can avoid limitations poor atom economy harsh reaction conditions.In this review, recent strategies compounds using tandem cyclization are summarized.

Язык: Английский

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Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(9), С. 2001 - 2014

Опубликована: Янв. 1, 2023

Excellent diastereoselective access to spirobenzo[ b ]oxepines via a [5 + 2] spirocyclization reaction of ortho -hydroxyacetophenones and 2-aroyl-1-chlorocyclopropanecarboxylates triggered by Cs 2 CO 3 was developed.

Язык: Английский

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Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Synthesis, Год журнала: 2024, Номер 56(10), С. 1619 - 1647

Опубликована: Фев. 15, 2024

Abstract This paper describes the versatility of substituted [(allyl­oxy)methyl]phosphonates to open way synthesis original phosphonated molecules with heterocyclic architectures. In 1,3-dipolar cycloaddition reactions nitrile oxides, imines, and nitrones, these [(allyloxy)methyl]phosphonates react as dipolarophiles give, regioselectively, corresponding isoxazolines, pyrazolines, isoxazolidines. Transition-metal-catalyzed reactions, including inter- or intramolecular Heck coupling, provided access cinnamyl- indenyl-linked moieties benzo-fused oxacycles, respectively. Additionally, ring-closing metathesis enabled 2,5-dihydrofurans phosphonate group at anomeric position. this work, 51 novel phosphorylated compounds, which may find significance in pharmaceutical agrochemical fields, were prepared.

Язык: Английский

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