Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(17), С. 2049 - 2055

Опубликована: Май 7, 2024

Comprehensive Summary An electrocatalytic multicomponent cascade cross‐coupling for the synthesis of chalcogenosulfonates has been established. This approach does not require use transition metals, acids, and external oxidants. The gentle conditions tolerance to a wide variety functional groups permit derivatization complex indoles.

Язык: Английский

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Reductive N-Formylation of Nitroarenes Mediated by Rongalite

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7220 - 7224

Опубликована: Сен. 28, 2023

Herein, we disclose a straightforward approach to access transition-metal-free reductive N-formylation of nitroarenes. This reaction integrates the dual role rongalite, which acts as reductant and C1 building block concurrently. provides an alternative method for synthesis N-aryl formamides from nitroarenes, including construction C–N bond. The utility this protocol was demonstrated by scale-up late-stage functionalizations complex molecules.

Язык: Английский

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Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(12), С. 1360 - 1366

Опубликована: Фев. 23, 2024

Comprehensive Summary The conversion of CF 3 ‐alkenes to gem ‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use green and readily available reducing salt mediate these reactions remains be explored. In this work, a concise construction gem‐ difluoroalkenes, which requires neither catalyst nor metal agent, was established. Rongalite, safe inexpensive industrial product, employed as both radical initiator reductant. This procedure compatible with linear cyclic diaryliodonium salts, enabling wide variety substrates (>70 examples). utility approach demonstrated through gram‐scale synthesis efficient late‐stage functionalizations anti‐inflammatory drugs.

Язык: Английский

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Copper-Catalyzed Multicomponent Coupling Reaction of Primary Aromatic Amines, Rongalite, and Alkynes: Access to N-Aryl Propargylamines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8220 - 8229

Опубликована: Май 16, 2024

In this work, a practical copper-catalyzed multicomponent coupling reaction of primary aromatic amines, rongalite, and alkynes for the direct synthesis N-aryl propargylamines has been developed. This method could overcome substrate limitation in A3 reactions formaldehyde, alkynes. Mechanistic studies revealed that rongalite acts as not only active C1 unit but also accelerator to activate situ-generated N-arylmethanimines with is highly efficient features broad scope, well utility scale-up converting corresponding product into useful heterocyclic skeletons.

Язык: Английский

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Palladium-catalyzed domino cyclization/direct functionalization involving the insertion of SO₂

New Journal of Chemistry, Год журнала: 2024, Номер 48(12), С. 5101 - 5106

Опубликована: Янв. 1, 2024

A reductive cross-coupling strategy for the synthesis of sulfone-containing oxindoles was presented. Moreover, using amines instead alkyl bromides, a palladium-catalyzed domino cyclization/aminosulfonylation also established.

Язык: Английский

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Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4340 - 4345

Опубликована: Май 14, 2024

An unconventional [1 + 1 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur(II) synthons, a reductant first time. Mechanism investigation indicated that reaction involved self-mediated valence state change rongalite. By performing step-economical method, challenging C5-substituted 1,3-dithiane can be achieved under mild simple conditions.

Язык: Английский

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Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Chemistry - A European Journal, Год журнала: 2024, Номер 30(44)

Опубликована: Июль 22, 2024

Sulfur(VI)-based functional groups are popular scaffolds in a wide variety of research fields including synthetic and medicinal chemistry, as well chemical biology. The growing interest sulfur(VI)-containing molecules has motivated the scientific community to explore new methods synthesize modify them. Here, photocatalysis plays key role granting access types reactivity under mild reaction conditions. In this Perspective, we present selection works reported last six years focused on photocatalytic assembly sulfones, sulfonamides, sulfoximines. We addressed intermediates for each transformation, while discussing limitations strength points protocols. Future directions field finally presented.

Язык: Английский

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β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing has thus attracted considerable attention. Here, we introduce a protocol the preparation alkyl aryl sulfones under mild conditions. This employs β-thioamide sulfone as novel motif donor. It forms sulfinates situ basic conditions, which then undergo cross-coupling with intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

Язык: Английский

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Efficient Synthesis of 3,3′‐Spirooxindole γ‐Butyrolactone via Rongalite‐Mediated Domino Reductive Aldol and Spiro‐Lactonization Reactions

ChemistrySelect, Год журнала: 2025, Номер 10(6)

Опубликована: Фев. 1, 2025

Abstract In this study, we develop a novel methodology involving rongalite‐mediated domino reductive/aldol reaction, followed by spiro‐lactonization of 2‐oxoindolin‐3‐ylidene acetates/malonates in presence base to synthesis 3,3′‐spirooxindole γ ‐butyrolactone. The detail such as effect solvent, different and substrate has been carried out. Scale up is also done. Sodium hydroxymethanesulfinate dihydrate (rongalite) concurrently dual role context; it acts reducing agent well C1 synthon. This approach offers several advantages, being metal‐ catalyst‐free, simple reaction protocol, having wide scope, using water green providing good excellent yields the products under mild conditions.

Язык: Английский

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Construction of Thiochroman-4-ols through a (4 + 2) Annulation Strategy Using Allenyl Sulfones as Substrates

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

Опубликована: Апрель 11, 2025

Herein, we report an efficient and straightforward access to highly functionalized thiochroman-4-ol derivatives by the construction of S-C C-C bonds in a domino fashion. The methodology is based on (4 + 2) annulation reaction involving α-substituted allenyl sulfones aromatic thiolates displaying ortho α-ketoester group as substrates. anionic sulfur species were generated situ reduction corresponding disulfides, using Rongalite/K2CO3 system. practicality strategy was further demonstrated gram-scale synthesis, postmodifications, compatibility with other types electron-deficient allenes (allenoate allenone).

Язык: Английский

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