Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines DOI

Cheng-Jing Li,

Mengyu Liu, Zhonglin Wei

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 11, 2024

A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key the success of this practical protocol relies not only on a bifunctional role dithionite, that is, serving as radical initiator SO

Язык: Английский

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

Arshad Ali,

C.‐S. CHUNG, Jingru Wang

и другие.

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

Процитировано

0
Catalyst-Free Radical Dearomatization of Phenols with Aryldiazonium Tetrafluoroborates and DABCO·(SO2)2 DOI
Xingxian Zhang, Guanyinsheng Qiu, Shaoyu Li

и другие.

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Март 4, 2025

Abstract A catalyst-free, three-component dearomatization of phenols with aryldiazonium tetrafluoroborates and DABCO·(SO2)2 has been developed for the synthesis 4-(arylsulfonyl)cyclohex-2,5-dien-1-one scaffolds. This method offers mild reaction conditions high step efficiency, providing a green efficient strategy phenols. Mechanistic studies indicated that this transformation relies on tandem radical sulfur dioxide insertion process.

Язык: Английский

Процитировано

0
Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles DOI
Fei Chen,

Jun-Ya Guo,

Yunhong Jia

и другие.

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

Опубликована: Март 16, 2025

A photocatalytic radical sulfonarylation of N-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl addition/cyclization sequence has been developed. This method employs alcohols as the precursors β-carbonyl alkyl radicals and Na2S2O5 cheap source sulfur dioxide. By using this procedure, wide variety γ-keto-sulfone-substituted oxindoles were facilely synthesized.

Язык: Английский

Процитировано

0
Iron-Catalyzed Alkylative Aminosulfonylation of Alkenes and Alkynes via Radical-Anion Relay DOI
Xiaoya Hou, Bangkui Yu, Hanmin Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 19, 2025

A novel Fe-catalyzed alkylative aminosulfonylation of alkenes and alkynes with alkyl halides O-Ts activated hydroxylamines by using Na2S2O4 as a reductant sulfone source has been developed. The metal-electron-shuttle catalysis was discovered to be vital for the highly efficient generation sulfonyl radicals anions without requiring organometallic intermediates. This method provides access sulfonamides from easily available features broad substrate scope.

Язык: Английский

Процитировано

0
A photoinduced three‐component reaction of thianthrenium salts, DABCO·(SO2)2, and benzyl ether substituted alkenes DOI
Ji Zhang,

J N Cen,

Shengqing Ye

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(14), С. 3130 - 3137

Опубликована: Май 31, 2024

Abstract A photoinduced three‐component reaction of thianthrenium salts, DABCO ⋅ (SO 2 ) , and benzyl ether substituted alkenes is developed, affording δ‐hydroxylsulfones with good functional group tolerance. This transformation proceeds through an anti‐Markovnikov hydrosulfonylation under a mild condition. Mechanism studies indicates that this undergoes radical pathway involving sulfur dioxide insertion 1,5‐hydrogen transfer processes.

Язык: Английский

Процитировано

2
A three-component reaction of cyclobutanone oxime esters, sulfur dioxide and N-alkyl-N-methacryloyl benzamides DOI
Shengqing Ye, Zhuang Chen,

Jiajing Lv

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(45), С. 9021 - 9028

Опубликована: Янв. 1, 2023

A three-component reaction of cyclobutanone oxime esters, DABCO·(SO2)2 and N-alkyl-N-methacryloyl benzamides is described. This proceeds without the addition any oxidant or transition metal, affording sulfonyl-containing isoquinoline-1,3-(2H,4H)-diones in moderate to good yields. Various functional groups are tolerated well this transformation. Mechanistic studies suggest that a radical pathway involved, including β-scission, sulfur dioxide insertion, intramolecular cyclization processes.

Язык: Английский

Процитировано

1
Graphitic Carbon Nitride as a Metal‐Free Heterogeneous Semiconductor Photocatalyst for Fluoroalkylation Reactions DOI Creative Commons
Hao Wang,

Fukai Xie,

He Wang

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(13)

Опубликована: Март 13, 2024

Abstract The increasing use of fluorine‐containing bioactive molecules necessitates efficient strategies for fluorinated group installation. Despite the impressive development photoinduced radical fluoroalkylation as a powerful tool introducing fluorine, persistent issues, including recyclability and reaction specificity homogeneous photocatalysts, still leave great room further advancement in sustainable general fashion. Herein, we report conceptually different approach toward multiple types fluoroalkylations by using recoverable versatile graphitic carbon nitride (g‐CN) nanosheets heterogeneous photocatalyst. This photocatalytic system enables diverse intermolecular alkenes with fluoroalkanesulfinates intramolecular fluoroalkyl migrations alkenyl triflates. Detailed characterizations mechanism studies substantiate stability this organic semiconductor crucial role photogenerated electron‐hole pairs.

Язык: Английский

Процитировано

0
Copper-catalyzed sulfonamidation of enol silyl ether via SO2 insertion towards the synthesis of β-keto sulfonamides DOI

Qinqiong Zeng,

Yujia Gong,

Xuemei Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(13), С. 3589 - 3595

Опубликована: Янв. 1, 2024

This method offers a simple, effective pathway for synthesizing diverse β-keto sulfonamides with satisfactory yields under mild conditions, showing broad substrate compatibility and good tolerance towards various functional groups.

Язык: Английский

Процитировано

0
Brønsted base catalyzed Reppe sulfonylation reaction DOI
X. He, Xiaohong Wang, Fei Zhou

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4740 - 4747

Опубликована: Янв. 1, 2024

The Reppe sulfonylation reaction has remained substantially underexplored. We present a novel method for involving SO 2 insertion, remarkably without the need metal catalysts, instead utilizing Brønsted bases as catalysts.

Язык: Английский

Процитировано

0
New Approach to Perthiyl Radicals for the Synthesis of Unsymmetric Disulfides DOI
Zhong Lian,

Fei Zhou,

X. He

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Июль 9, 2024

Abstract Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report a novel transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks inaugural use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process were verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously.

Язык: Английский

Процитировано

0