Electrooxidative S-Sulfoximination of Sulfenamide: A Metal-/Catalyst-Free Green Approach

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

Herein, we present a metal-/catalyst-free, novel approach for S-sulfoximination of sulfenamide. The electrooxidative reactions sulfenamides and sulfoximines are fast, high-yielding, atom-economical (99.5%), broad-substrate-tolerant, free from supporting electrolytes. protocol is ecofriendly shows wider substrate tolerance than previous reports. drug-attached sulfenamide (levetiracetam) sulfoximine (albendazole) also undergo the reaction efficiently. A possible mechanistic pathway proposed. Fascinatingly, target products obtained via photochemical in presence photocatalyst eosin Y.

Language: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Microfluidic Photocatalytic Ring Expansion of Sulfonium Salts for the Synthesis of Cyclic Sulfides

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6507 - 6513

Published: April 6, 2025

Cyclic sulfides are relevant building blocks in medicinal and synthetic chemistry, with applications ranging from drug discovery to materials science. However, the synthesis of medium-sized cyclic (6-8-membered rings) remains largely underdeveloped. Herein, we report a photocatalytic ring-expansion strategy for sulfonium salts, granting access six-, seven-, eight-membered very high regio- diastereocontrol. The implementation method under continuous flow was key increasing efficiency minimizing product decomposition. Mechanistic investigations revealed formation benzylic radicals carbocation intermediates that control diastereoselectivity observed. Finally, utility this approach demonstrated sulfoxides sulfones, which can be easily obtained corresponding sulfide products.

Language: Английский

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Palladium-Catalyzed Amino-Sulfonylation of Aryl Iodide Derivatives via the Insertion of Sulfur Dioxide: One-Pot Synthesis of Aryl Primary Sulfonamides with Thiourea Dioxides

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: June 10, 2024

Abstract A palladium-catalyzed one-pot amino-sulfonylation of aryl iodide derivatives with thiourea dioxide, PdCl2dppf, and added hydroxylamine-O-sulfonic acid is presented. This gave structure diversity to primary sulfonamides features good functional group compatibility, mild reaction conditions, excellent regioselectivity, moderate yields. The robustness potential this method have also been successfully demonstrated by late-stage elaboration gram-scale reaction. approach achieves the divergent construction complex core structures that are prevalent in highly valuable natural products such as Sulpiride, Venetoclax, Furosemide­.

Language: Английский

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Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: July 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.

Language: Английский

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Synthesis of Sulfonimidamide‐Based 1,2‐Benzothiazines by [4+2] Oxidative Annulation of Sulfonimidamides and Alkynes in Water under Visible Light

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(6)

Published: Jan. 5, 2024

Abstract Herein, we disclose a visible‐light‐induced rhodium‐catalyzed oxidative C−H/N−H bond activation of sulfonimidamides (SIAs) and subsequent [4+2] annulation with an alkyne in water to yield SIA‐based 1,2‐benzothiazines good high yields short reaction times. Further, the C=C benzothiazine can be cleaved under environmentally friendly conditions (oxygen atmosphere blue LEDs) deliver o ‐acyl‐ N ‐acyl SIAs. Interestingly, SIAs also synthesized directly from very without isolating benzothiazine. The selective efficient reduction presence InCl 3 /R SiH led formation hitherto unknown dihydro‐1,2‐benzothiazine quantitative yield.

Language: Английский

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Ni-Catalyzed Mild Synthesis of Sulfonylurea via Tandem Coupling of Sulfonyl Azide, Isocyanide, and Water

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7477 - 7482

Published: May 10, 2023

An efficient, mild, and novel route is developed to synthesize sulfonylurea via the nickel-catalyzed tandem coupling of sulfonyl azide, isocyanide, water in aqueous media. The azide expected act as a nitrene precursor, which upon reaction with isocyanide generates carbodiimide. Herein, acts nucleophile reacts carbodiimide deliver product. protocol uses an inexpensive nickel catalyst, environmentally friendly (as nucleophile), room temperature provides products moderate good yields.

Language: Английский

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One-pot synthesis of α-sulfoximinophosphonate via Kabachnik–Fields reaction

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(35), P. 7036 - 7039

Published: Jan. 1, 2022

Hitherto unknown α-sulfoximinophosphonates are synthesized via the Kabachnik–Fields reaction with imine (sulfoximine) as a nucleophile for first time.

Language: Английский

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Photomediated Tandem Sulfonyl Addition–Chemoselective N-Cyclization of o-Alkenyl Aryl Ureas: Direct Assembly of Functionalized Dihydroquinazolinones

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(14), P. 9414 - 9418

Published: July 6, 2022

Photoredox-mediated tandem addition–chemoselective cyclization of o-alkenyl aryl ureas is reported for the synthesis sulfonyl and activated alkyl-decorated dihydroquinazolinones. By a careful choice urea starting materials, we achieved chemoselective N-cyclization in presence more reactive amidic oxygen. We have demonstrated scope methodology with variety chlorides alkyl halides. Finally, large-scale sulfonyl-substituted dihydroquinazolinone showcases synthetic utility methodology.

Language: Английский

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Immobilized Rose Bengal as Photocatalyst for Metal‐Free Thiocyanation of Azaheterocycles under Continuous Flow Conditions

Helvetica Chimica Acta, Journal Year: 2023, Volume and Issue: 106(10)

Published: Sept. 13, 2023

Abstract The immobilization of Rose Bengal onto Merrifield resin and its application in the light‐driven metal‐free thiocyanation azaheterocycles continuo were investigated. supported photocatalyst was used batch reactions under heterogeneous conditions, with different azaheterocycles, proved to efficiently promote reaction. Its recovery recycle also demonstrated for up four times. resin‐supported then employed continuous flow affording thiocyanate functionalized higher space‐time‐yields than in‐batch transformations, a shorter reaction time. easily modification SCN groups by synthetizing trifluoromethyl thioethers sulfenyl tetrazoles derivates high yields.

Language: Английский

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