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

Yuping Luo,

Xiujuan He,

Yike Jiang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11766 - 11776

Опубликована: Авг. 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.

Язык: Английский

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

Padma Priya V. R,

S. Sugapriya,

Antony Haritha Mercy A

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0
Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides DOI
Xuebin Yan, Rui Zhao, Yu‐Hang Miao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

0
Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts DOI
Xiangyu Zhuang, Hao Li,

Zhaoyu Feng

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 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.

Язык: Английский

Процитировано

0
A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide DOI

Padma Priya V. R,

Antony Haritha Mercy A,

N. Kannan

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16426 - 16432

Опубликована: Окт. 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.

Язык: Английский

Процитировано

1
Trideuteromethylthiolation through Reaction of Arynes, S-Methyl-d3 Sulfonothioate with Sulfonamides or Amides: Access to Trideuteromethylated Sulfilimines DOI

Yuping Luo,

Xiujuan He,

Yike Jiang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11766 - 11776

Опубликована: Авг. 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.

Язык: Английский

Процитировано

0