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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Hydro-phosphorothiolation of Styrene and Cyclopropane with S-Hydrogen Phosphorothioates under Ambient Conditions

Organic Letters, Год журнала: 2024, Номер 26(24), С. 5141 - 5145

Опубликована: Июнь 7, 2024

A metal-free hexafluoroisopropanol-mediated hydro-phosphorothiolation of styrenes and donor-acceptor cyclopropanes with

Язык: Английский

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Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4947 - 4957

Опубликована: Март 18, 2024

A photoredox/copper-catalyzed cascade radical cyclization/phosphorothiolation reaction of N-allylbromoacetamides and P(O)SH compounds has been established. broad range novel nonfluorine- or difluoro-substituted 2-pyrrolidinones bearing the C(sp3)-SP(O)(OR)2 moiety can be conveniently constructed in moderate to good yields under mild conditions. Importantly, most tested phosphorothiolated showed potent inhibitory effects toward both AChE BChE.

Язык: Английский

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Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of sulfonium salts with S₈, H-phosphonates or P₄S₁₀, and alcohols

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5731 - 5740

Опубликована: Янв. 1, 2024

A simple and practical method for the synthesis of S -alkyl phosphorothioates/phosphorodithioates through three-component reaction cyclic sulfonium salts with 8 , H -phosphonates, or P 4 10 alcohols was readily developed.

Язык: Английский

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Recent Advances on Direct Phosphorothiolation Reactions

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июль 23, 2024

Abstract Organophosphorothioates are organic molecules containing sulfur and phosphorus, with significant biological activity physicochemical properties, widely used in synthesis, medicinal chemistry, the agrochemical industry. In particular, many phosphorothioates display a variety of activities, such as antifungal, antibacterial, anti‐parasite, anticancer, so on. Traditionally, synthesis has mainly relied on indirect methods involving construction S−P bond. recent years, direct phosphorothiolation gained attention reliable rapid method for introducing −S−P(O)(OR) 2 group into parent molecules. This article reviews latest advances reactions, categorized based different sources group.

Язык: Английский

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Additive-free, N-chlorosuccinimide-promoted electrophilic phosphorothiolation/cyclization of alkynes with P(O)SH compounds to access heterocyclic phosphorothiolated molecules

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5841 - 5846

Опубликована: Янв. 1, 2024

A N -chlorosuccinimide-promoted electrophilic phosphorothiolation/cyclization of alkynes for the construction phosphorothiolated heterocycles under metal- and additive-free conditions has been developed.

Язык: Английский

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Visible-Light-Induced Phosphorothioation of Alkenyl Sulfonium Salts with S₈ and H-Phosphonates

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

Опубликована: Фев. 4, 2025

An efficient and practical method for synthesizing vinyl phosphorothioates has been demonstrated through a visible-light-induced three-component reaction of alkenyl sulfonium salts, S8, H-phosphonates. This facilitates the synthesis diverse range with wide substrate scope functional group tolerance. Preliminary mechanistic studies suggest that involves phosphorothioate radical-triggered process.

Язык: Английский

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Radical 1,2-fluoroalkylation/stannylation of terminal alkynes

Journal of Fluorine Chemistry, Год журнала: 2025, Номер 283-284, С. 110422 - 110422

Опубликована: Март 23, 2025

Язык: Английский

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Dual Photoredox/Copper‐Catalyzed 1,2‐Diphosphorothiolation of Alkenes with P(O)SH Compounds to Access Vicinal Bisphosphorothioates

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 12, 2025

Comprehensive Summary An efficient photoredox/copper dual‐catalyzed 1,2‐diphosphorothiolation of alkenes with P(O)SH compounds was realized under oxidative conditions. In this transformation, acted as both the phosphorothioate radical source and coupling partner. A wide range valuable vicinal bisphosphorothioates can be easily constructed starting from simple raw materials in a step‐ atom‐economical manner. Notably, reaction system has been successfully used to incorporate two groups into many drug molecules, highlighting substantial synthetic potential protocol.

Язык: Английский

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Reactions of alkynes with C–S bond formation: recent developments

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(32), С. 6443 - 6484

Опубликована: Янв. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

Язык: Английский

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