Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2758 - 2763

Published: April 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.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4947 - 4957

Published: March 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.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5141 - 5145

Published: June 7, 2024

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

Language: 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, Journal Year: 2024, Volume and Issue: 11(20), P. 5731 - 5740

Published: Jan. 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.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 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.

Language: Английский

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Radical 1,2-fluoroalkylation/stannylation of terminal alkynes

Journal of Fluorine Chemistry, Journal Year: 2025, Volume and Issue: 283-284, P. 110422 - 110422

Published: March 23, 2025

Language: Английский

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Recent Advances on Direct Phosphorothiolation Reactions

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 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.

Language: Английский

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Photoredox/Copper Dual-Catalyzed Phosphorothiolation of Propargylic Derivatives for the Switchable Synthesis of S-Alkyl, S-Vinyl and S-Allenyl Phosphorothioates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7049 - 7054

Published: Aug. 9, 2024

Herein, we report a photoredox/copper dual-catalyzed selective phosphorothiolation of propargylic derivatives from easily accessible [P(O)SH] compounds. This reaction provides general, mild and versatile procedure to synthesize variety synthetically useful

Language: 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, Journal Year: 2024, Volume and Issue: 11(20), P. 5841 - 5846

Published: Jan. 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.

Language: Английский

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Elemental Sulfur/Selenium-Mediated Metal-Free Phosphinothioation and Phosphinoselenoation of Vinylsulfonium Salts with P–H Bonds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

An efficient and facile method has been developed for the construction of novel P–S–C P–Se–C bonds by facilitating three-component cross-coupling reaction P–H with elemental sulfur/selenium vinylsulfonium salts, utilizing sodium bicarbonate as a base. This approach eliminates need use toxic odorous active reagents noble metals, thereby offering new pathway synthesizing S-phosphinothioates Se-phosphinoselenoates via organic conversion inorganic sources. The showcased remarkable versatility in terms substrate applicability, particularly organophosphorus compounds containing salt derivatives. resulting phosphinothioation/phosphinoselenoation products can be obtained high yield regioselectivity. Additionally, plausible mechanism this transformation proposed based on step-by-step control experiments 31P NMR tracking analysis.

Language: Английский

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