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

Cheng-Jing Li,

Mengyu Liu, Zhonglin Wei

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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

Language: Английский

Radical‐Polar Crossover Bicyclization Enables a Modular Synthesis of Saturated Bicyclic Amines DOI Creative Commons

Feng Danqing,

Xiao Geng,

Lingling Zuo

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

Abstract The rapid assembly of diverse cyclic amines from simple precursors is now considered as an ideal platform with respect to efficiency and sustainability. To date, numerous synthetic methods have been successfully developed however, most them are limited a narrow subset amines, variations in ring size often requiring different substrates distinct strategies. Furthermore, the “escape‐from‐Flatland” concept has led chemists focus on synthesis C(sp 3 )‐rich small molecules for potential drug candidates. Herein, successful realization radical‐polar crossover bicyclization reaction reported easily available cyclopropylamines substituted alkenes through photoredox catalysis. This approach introduces innovative methodology de novo collection 4/5‐, 5/5‐, 6/5‐,7/5‐, 5/6‐fused saturated bicyclic systematic modular manner excellent diastereoselectivity. work highlights utility photoinduced radical–polar bicyclization, applicability which showcased by functional group tolerance, wide substrate scopes, derivatization reactions.

Language: Английский

Citations

1

Synthesis of constrained bicycloalkanes through bibase-promoted brook rearrangement/radical-polar crossover cyclization DOI Creative Commons

Xinke Ouyang,

Bingyao Shi,

Yuanyuan Zhao

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(28), P. 11092 - 11098

Published: Jan. 1, 2024

A concise protocol for the synthesis of constrained bicycloalkanes has been developed, using easily obtainable α-silyl alcohols and alkenes through a bibase-promoted brook rearrangement/radical-polar crossover cyclization (RPCC) process.

Language: Английский

Citations

4

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

Arshad Ali,

C.‐S. CHUNG, Jingru Wang

et al.

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

Published: Jan. 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.

Language: Английский

Citations

0

DABSO-Mediated Hydrosulfonylation of Activated Alkenes DOI
Xiaoxiao Yang,

Shuaiqi Lu,

Yongxin Zhang

et al.

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

Published: May 7, 2025

Highly functionalized sulfone containing scaffolds are ubiquitous and attracting increasing interest in pharmaceutical agrochemicals owing to their enhanced activities. Herein, we present an alternative protocol access highly substituted sulfones from readily accessible olefin feedstocks sulfinate salts through a DABSO enabled anti-Markovnikov hydrosulfonylation process. Notably, the practical procedure features excellent compatibility with various susceptible functional groups broad substrate scope under mild operationally simple conditions. Gram-scale preparation, post-functionalization of complex molecules, applications synthesis bioactive compounds underscore potential drug discovery.

Language: Английский

Citations

0

Electrochemical Synthesis of Vinyl, Alkyl, and Allyl Sulfones from Sodium Sulfinates and Olefins DOI

Pengkai Fang,

Qingxu Wang,

Xiaoqian Shen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12619 - 12627

Published: Aug. 16, 2024

An electrochemical synthesis of vinyl, alkyl, and allyl sulfones using sodium sulfinates olefins was reported. This method uses direct current to pass through an undivided cell equipped with graphite carbon electrodes, a series diverse sulfone compounds can be synthesized at room temperature in high yields.

Language: Английский

Citations

3

Transition-Metal-Catalyzed Regiodivergent Sulfonylation of Aziridrines for the Synthesis of β‑Amino Sulfones DOI

Qinqiong Zeng,

Yujia Gong,

X. He

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(22), P. 6340 - 6346

Published: Jan. 1, 2024

We developed the first transition-metal-catalyzed, regiodivergent sulfonylation of aziridines, enabling efficient synthesis diverse β-amino sulfones under mild conditions with broad substrate compatibility and high regioselectivity.

Language: Английский

Citations

3

Light-Induced 1,3-Thiosulfonylation of β,γ-Unsaturated Ketones with Thiosulfonates DOI

Jiuwen Xu,

Bo-Xi Liu,

Xinyu Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6798 - 6802

Published: Aug. 7, 2024

Sulfur-containing compounds exhibit potent significance in drug molecules. Thiosulfonates as 1,3-thiosulfonylation reactants to olefins have yet be investigated. Herein, we report photoinduced 1,3-difunctionalization of β,γ-unsaturated ketones with thiosulfonates, which undergo a radical 1,2-acyl shift. The protocol features mild conditions, high regioselectivity, and 100% atom economy.

Language: Английский

Citations

2

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2

Advances in the Synthesis of Sulfur-Containing Cyclic Architectures via Insertion of SO2 DOI
Chao Shu,

Xi Lu,

Yuyang Huang

et al.

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

Published: April 6, 2024

Abstract Sulfur-containing heterocycles, where the S(R) moiety is located within cyclic structure, have found tremendous applications in fields of chemical, pharmaceutical, and materials sciences due to their unique biological pharmaceutical activities. Recent years witnessed increasing interest sulfur-containing new methods for synthesis been reported by adopting modern methodologies technologies through insertion sulfur dioxide. The main objective this Account overview latest major developments on heterocyclic systems, mainly covering thermo-, photo- electron-induced cyclization dioxide (SO2). We aim provide readership with a comprehensive understanding topic offer positive outlook promising future field. 1 Introduction 2 Thermal-Induced Cyclization 3 Photoinduced Radical 4 Electron-Induced 5 Conclusion

Language: Английский

Citations

1

Photoredox-catalyzed sulfonylation of diaryliodonium salts with DABSO and silyl enolates involving the insertion of SO2 DOI Creative Commons
Shuoshuo Zhang, Qian Zhang,

Shuizhen Lin

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(21), P. 14697 - 14701

Published: Jan. 1, 2024

A versatile photoredox-catalyzed three-component sulfonylation of diaryliodonium salts with DABSO and silyl enolates involving the insertion SO2 was developed. Moreover, by employing β-alkyl substituted as substrates, would give α-alkyl β-keto sulfones, which are difficult to accessed previous method SO2.

Language: Английский

Citations

1