Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Язык: Английский

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Phototriggered Self-Catalyzed Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 19, 2024

A highly effective external photocatalyst- and additive-free method for the phosphorylation of 3,4-dihydroquinoxalin-2(1

Язык: Английский

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Photocatalytic Sulfonylation: Innovations and Applications

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Язык: Английский

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Photoinduced Dehydrogenative Amination of Quinoxalin-2(1H)-ones with Air as an Oxidant

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5371 - 5381

Опубликована: Март 29, 2024

A facile and eco-friendly photoinduced dehydrogenative amination of quinoxalin-2(1H)-ones with aliphatic amines without any metal, strong oxidant, photocatalyst has been established for the first time. This reaction proceeding efficiently air as sole oxidant at room temperature obtains a wide range 3-aminoquinoxaline-2(1H)-ones in high yields excellent functional group tolerance. The mechanistic studies show an interesting involvement photosensitizer, which eliminates requirement external photocatalysts.

Язык: Английский

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Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2758 - 2763

Опубликована: Апрель 24, 2024

Abstract Herein, we present a (NH 4 ) 2 S O 8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis various phosphorothioate‐containing quinoxalin‐2(1 H )‐one derivatives (46 examples) in 37–79% yields. The is compatible range functional groups easily adaptable to large‐scale synthesis. Preliminary studies suggest involvement phosphorothioate radicals these transformations.

Язык: Английский

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Recyclable V₂O₅/g-C₃N₄ Heterojunction-Catalyzed Visible-Light-Promoted C3–H Trifluoromethylation of Quinoxalin-2-(1H)-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9543 - 9550

Опубликована: Июнь 14, 2024

A visible-light-initiated C-H trifluoromethylation of quinoxalin-2(1

Язык: Английский

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Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)-ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes

Organic Letters, Год журнала: 2024, Номер 26(26), С. 5482 - 5487

Опубликована: Июнь 24, 2024

An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition bicyclo[1.1.0]butanes and quinoxalin-2(1H)-ones, facilitated by Lewis acid catalysis, is presented. This reaction carried out under mild conditions exhibits a broad substrate scope excellent functional group tolerance.

Язык: Английский

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Arylcyanation of Styrenes by Photoactive Electron Donor–Acceptor Complexes/Copper Catalysis

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7949 - 7955

Опубликована: Сен. 11, 2024

A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between photoactive EDA complex dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm participation complexes as reactive intermediates. This three-component process smoothly in presence pharmaceutically relevant core structures sensitive functional groups, which offers possibility precise editing drug molecules with important scaffolds.

Язык: Английский

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Construction of β-Oximino Phosphorodithioates via (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl-Promoted Difunctionalization of Alkenes with tert-Butyl Nitrite, P₄S₁₀, and Alcohols

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3883 - 3888

Опубликована: Апрель 29, 2024

A (2,2,6,6-tetramethylpiperidin-1-yl)oxyl-mediated difunctionalization of alkenes with

Язык: Английский

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Visible-Light-Promoted Deoxygenative Alkylation of Quinoxalin-2(1H)-ones with Activated Alcohols

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6334 - 6344

Опубликована: Апрель 15, 2024

A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.

Язык: Английский

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