Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Язык: Английский

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Polysulfide synthesisviavisible-light-induced heteroarene-migratory dithiosulfonylation reaction

Chemical Communications, Год журнала: 2023, Номер 59(47), С. 7247 - 7250

Опубликована: Янв. 1, 2023

A visible-light-induced radical cascade heteroarene-migratory dithiosulfonylation has been developed to synthesize polysulfides, which can be transformed into dihydrothiophene and homoallyl disulfide derivatives.

Язык: Английский

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Visible-Light Photocatalytic Synthesis of Difluoromethylated Selenides from Selenosulfonates through a Radical Process

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12658 - 12667

Опубликована: Авг. 18, 2023

A photocatalytic synthesis of difluoromethylated selenides from selenosulfonates is described here. Bench-stable difluoromethyl phosphonium salt [Ph3PCF2H]Br reacts smoothly with to give a series functionalized in moderate good yields via radical process. This protocol free stoichiometric base and reductant, has tolerance functional groups, successful late-stage modification bioactive molecules, which provides facile access molecules pharmaceutical relevance.

Язык: Английский

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Simultaneous Preparation of Sulfides/Selenides and Sulfones via Synergistic Nickel-Catalyzed Reductive Coupling and S_N2 Reaction

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9207 - 9212

Опубликована: Дек. 19, 2023

Sulfone compounds and thioether are two highly valuable classes of compounds, but it is challenging to prepare sulfone simultaneously efficiently. Here we report that sulfides/selenides sulfones can be obtained using allyl bromide/benzyl bromide-activated alkyl bromides thiosulfonates/selenosulfonates a nickel-catalyzed reductive coupling SN2 synergistic strategy, which characterized by excellent atom step economy, mild reaction conditions, broad functional group compatibility, yields.

Язык: Английский

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Four-Component Radical 1,2-Selenosulfonylation of Allenes

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5705 - 5712

Опубликована: Июнь 27, 2024

Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides the complex selenosulfones. This is first case achieving 1,2-selenosulfonylation via process, wherein precise control rates polarity matching enhance high regioselective conversion. The conditions are ecofriendly mild with step-efficiency by forming two new C–S bonds one C–Se bond pot. Moreover, can be achieved replacing esters aryldiazonium tetrafluoroborates this system.

Язык: Английский

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

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

Опубликована: Апрель 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.

Язык: Английский

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Cu-catalyzed efficient construction of S (Se)-containing functional organosilicon compounds

Chemical Communications, Год журнала: 2022, Номер 58(90), С. 12564 - 12567

Опубликована: Янв. 1, 2022

A Cu-catalyzed cascade reaction of four-membered silacyclobutanes (SCBs) and thiosulfonates to construct S (Se)-containing organosilicon compounds was developed. The protocol shows a wide range substrate scope, high functional group compatibility mild conditions. New C-S (Se) Si-O bonds were constructed in one step.

Язык: Английский

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Vicinal Difunctionalization of Unactivated Alkenes Through Radical Addition/Remote (Hetero)Aryl Migration Cascade

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(43)

Опубликована: Сен. 9, 2024

Abstract Alkenes are ubiquitous in natural and synthetic molecules constitute versatile building blocks. Remarkably, their radical 1,2‐difunctionalization offers a valuable tool for rapidly accessing multifunctional compounds through step atom‐ economy process. More particularly, the addition of (hetero)aromatic groups onto alkenes is particular appeal given numerous applications aromatic various fields. However, such process becomes difficult when attempted on simple non‐conjugated aliphatic (unactivated alkenes). In this context, (hetero)arylation unactivated functionalization followed by remote (hetero)aryl migration has recently emerged as powerful opportunity to address lack reactivity π systems. The advances chemistry have led flood methods trigger carbon‐ or heteroatom‐centered radical/(hetero)aryl sequence. Interestingly, ring can take place from atoms. This feature spurred design several substrates allowing occur. review intends provide an overview contributions according type that been employed. reaction scope, limitations mechanistic aspect will be discussed with aim stimulating efforts research area.

Язык: Английский

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Catalyst‐Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible‐Light‐Induced Charge Transfer

Chemistry - A European Journal, Год журнала: 2022, Номер 28(15)

Опубликована: Фев. 3, 2022

We report a visible-light-induced three-component sulfonyl-heteroarylation of vinyl ethers with sulfinates and five-membered heteroaryl chlorides. This protocol proceeds via electron-donor-acceptor (EDA) complexes between chlorides, giving β-sulfonyl alkyl heteroarenes high efficiency excellent regioselectivity under mild catalyst-free conditions. Utilization CF3 SO2 Na or CF2 HSO2 as coupling partners further achieves fluoromethyl-arylation ethers, furnishing series valuable /CF2 H-incorporated heterocycles

Язык: Английский

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Research Progress in Synthesis and Application of Thiosulfonates

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(8), С. 2322 - 2322

Опубликована: Янв. 1, 2022

As an important kind of synthons, thiosulfonates can react with alkynes, alkenes, aldehydes, and halogenated hydrocarbons to synthesize thioethers sulfones.At the same time, some thiosulfonate compounds have anti-viral anti-fungal bioactivities.The synthesis their applications in organic been under spotlight.Thus, according different types catalysts new progress green chemistry, is summarized.On other hand, reactants reaction types, application reviewed.In future, among researches on construction sulfides thiosulfonates, various difunctionalization reactions are still promising directions.

Язык: Английский

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