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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Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of N-allylbromoacetamides toward the synthesis 2-pyrrolidinone derivatives has been developed with arylboronic acids as reaction partner. This proceeds through a sequential single-electron-transfer pathway via 5-exo-trig cyclization carbonyl insertion steps, furnishing variety in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied CO source here nickel catalyst, which provides supplement for carbonylation chemistry heterocycle synthesis.

Язык: 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, Год журнала: 2024, Номер 26(33), С. 7049 - 7054

Опубликована: Авг. 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

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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NHC Catalyzed Radical Tandem Cyclization: An Efficient Synthesis of α,α-Difluoro-γ-lactam Derivatives

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(34), С. 6988 - 6998

Опубликована: Янв. 1, 2024

Herein, an N-heterocyclic carbene (NHC) catalyzed radical tandem cyclization reaction of

Язык: Английский

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³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 5, 2024

Abstract 31 P NMR spectroscopy is a consolidated tool for the characterization of organophosphorus compounds and, more recently, reaction monitoring. The evolution organic synthesis, mainly due to combination elaborated building blocks with enabling technologies, generated great challenges understand and optimize synthetic methodologies. In this sense, experiments also became routine technique monitoring, accessing products side yields, chiral recognition, kinetic data, intermediates, as well basic parameters, such acid‐base hydrogen‐bonding. This review deals these aspects demonstrating essential role spectroscopy. recent publications (the last ten years) will be explored, discussing strategies accomplished detect and/or quantify distinct molecules, approaching mechanism, stability, stereochemistry, utility probe.

Язык: Английский

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New Frontiers in Phosphorothioate Formation: Harnessing Inorganic Phosphorus Sources

Chemical Communications, Год журнала: 2024, Номер 60(99), С. 14691 - 14702

Опубликована: Янв. 1, 2024

This review highlights the latest advancements in synthesis of phosphorothioates and their derivatives from inorganic phosphorus sources, focusing on applicability, mechanisms, current limitations, potential future directions.

Язык: Английский

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