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
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
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
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
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
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
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
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
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
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
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