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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Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

The functionalization of N-acylsulfenamides is a research focus in organosulfur chemistry, as the N-S array has unique properties and versatile applications. Although great progress been made S-functionalization, N-functionalization, especially N-arylation N-acylsulfenamides, rarely explored because lower nucleophilicity N-site. Herein, we report Brønsted acid-catalyzed regioselective reaction with o-quinone diimides. Under mild metal-free conditions, wide range N-arylated have prepared good yields excellent regioselectivity. ease gram-scale synthesis transformations into useful sulfonamides demonstrates their synthetic practicality.

Language: Английский

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Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

The site-selective incorporation of sulfilimine functionalities into aromatic compounds provides a vital strategy for drug discovery in medicinal chemistry. However, green and sustainable methods realizing the goal are still limited. Here, we report copper-catalyzed S-arylation sulfenamides with aryl thianthrenium salts irradiated by visible light without photocatalyst, which exhibited fine functional-group compatibility gave desired products high yields. Mechanistic investigations revealed that key to achieving these results is generation an electron donor-acceptor (EDA) complex between under basic conditions.

Language: Английский

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Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 20, 2025

We herein disclose a mild metal-free strategy for the construction of heteroaryl-derived sulfilimines. Central to this approach is in situ generated sulfinimidoyl fluoride intermediate that exhibits an optimal balance reactivity and stability efficient S(IV)-derived SuFEx reactions with heteroarenes without Lewis acids or base additives. This protocol enables rapid incorporation broad range afford diverse sulfilimine scaffolds potent antimicrobial activities against plant pathogens.

Language: Английский

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Recent advances in haloarene synthesis by aryne reactions

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100136 - 100136

Published: May 1, 2025

Language: Английский

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A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16426 - 16432

Published: Oct. 31, 2024

We develop a rapid and mild protocol to access sulfonimidoyl fluoride-[S(VI)] from sulfenamide-[S(II)] directly. The transformation occurs via the reaction of sulfenamide with NCS (N-chlorosuccinimide), water, TBAF in acetonitrile. Water act as source for S═O bond formation fluoride, respectively. takes very short time (within 5 min). drug molecules, such Carbamazepine Levetiracetam attached fluorides are also achieved following this protocol. Furthermore, fluoride is transformed into sulfonimidamide presence AlCl3. To best our knowledge, it first report detailing synthesis directly S(II)-sulfenamide.

Language: Английский

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Trideuteromethylthiolation through Reaction of Arynes, S-Methyl-d₃ Sulfonothioate with Sulfonamides or Amides: Access to Trideuteromethylated Sulfilimines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11766 - 11776

Published: Aug. 3, 2024

A direct and practical three-component tandem reaction of arynes, S-methyl-d3 sulfonothioate with sulfonamides or amides is developed. The highly efficient chemoselective, which allows mild synthesis trideuteromethylated sulfilimines broad substrate scope good functional group compatibility, giving the products in to excellent yields 92%–99% deuterium incorporation. Mechanism studies disclosed sulfenamide that generated situ key intermediate for reaction. This protocol provides potential method introduction -SCD3 moiety deuteration marked drugs drug candidates containing sulfilimine skeleton.

Language: Английский

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