Alkoxy Radical‐Triggered 1,1,2‐Trifunctionalization of Unactivated Alkenes towards N,O‐Spiroaminals

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Comprehensive Summary N,O‐Spiroaminals have potential biological activities and abilities to modulate the physicochemical pharmacokinetic properties of drug molecules. However, effective catalytic methods for efficient construction N,O‐spiroaminals are still limited date. Herein, we report a novel 1,1,2‐trifunctionalization unactivated alkenes rapidly efficiently obtain diverse array architecturally intriguing N,O‐spiroaminals. This methodology exhibits broad substrate scope, good functional group compatibility, synthetic utility by scale‐up reaction, product derivatizations late‐stage functionalization complex biorelevant molecule. Notably, this transformation selectively allows formation three new chemical bonds (C–O, C–C, C–N) one spiro quaternary carbon center across C‐C double bonds.

Language: Английский

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Iron‐Mediated Desulfonylative Cross‐Electrophile Couplings of Heteroaryl Sulfones with Thiosulfonates for Efficient Synthesis of Heteroaryl Sulfides

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Comprehensive Summary A desulfonylative thiolation between heteroaryl sulfones and thiosulfonates for the efficient synthesis of sulfides was developed. The cross‐electrophile couplings proceeded effectively via old C–SO 2 bond cleavage new C–S formation in presence cheapest widely available iron powder as mediator under transition metal catalyst‐free conditions, leading to a wide array derived from benzo[ d ]thiazole, ]oxazole, thiazole, 1,3,4‐thiadiazole, 1 H ‐tetrazole modest excellent yields. In addition, reaction exhibited good functional group compatibility, protocol could also be applicable use selenosulfonate substrate subjected scale‐up with equal ease. Notably, unreacted readily recovered after by resorting attracting property magnetic stir bar iron.

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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Electrochemical Synthesis of Vinyl, Alkyl, and Allyl Sulfones from Sodium Sulfinates and Olefins

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12619 - 12627

Published: Aug. 16, 2024

An electrochemical synthesis of vinyl, alkyl, and allyl sulfones using sodium sulfinates olefins was reported. This method uses direct current to pass through an undivided cell equipped with graphite carbon electrodes, a series diverse sulfone compounds can be synthesized at room temperature in high yields.

Language: Английский

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Electrochemical Synthesis of Alkenylsulfonates from Alkynes, NaHSO₃ and Alcohols

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Comprehensive Summary Alkenylsulfonates are commonly encountered in medicinal chemistry, polymer and organic synthesis. In this research, an electrochemical reaction involving alkynes, NaHSO 3 , alcohols has been developed. This method yields functionalized alkenylsulfonates good with broad functional group tolerance. Mechanism studies indicate that anodic oxidation of inorganic sulfite, radical insertion process, HAT process involved transformation.

Language: Английский

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Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes

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

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

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