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
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3664 - 3674
Published: Feb. 21, 2024
Regioselective 1,2-dichalcogenation of alkenes has attracted significant attention in modern organic synthetic chemistry. While there are a plethora methods to access alkene dichalcogenated architectures, sulfonylsulfination is extremely challenging due the inherent characteristics sulfur atom. Herein, multicomponent fragment coupling alkenes, sulfinates, and DABSO was developed construct densely functionalized sulfonylsulfinated products, which otherwise access, with broad substrate scope group tolerance under mild operationally simple conditions, using an inexpensive 100–1000 ppm photocatalyst. In addition, protocol applied late-stage functionalization complex molecules, obtained products were converted into diverse downstream transformations demonstrate their potential. Experimental theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl sulfinyl oxygen radical mutual radical–polar crossover coupling. This strategy provides previously inaccessible good-to-high regio- stereoselectivity, along opening up unexplored directions.
Language: Английский
Citations
17
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3478 - 3483
Published: Aug. 23, 2023
Abstract Described herein is a visible light‐mediated radical addition/SO 2 insertion/anionic cyclization of benzo‐fused homoallylic tosylates, allowing access to diverse array otherwise challenging‐to‐access fluoromethylated polycyclic γ ‐sultines with two adjacent tetrasubstituted carbon stereocenters in 49–95% yields, which can be further readily functionalized towards bulky carbon‐containing ‐sultone and mercaptoalkanol. Sodium fluoroalkanesulfinates were utilized as bifunctionalization reagents for both fluoromethyl groups SO . The proceeds through stepwise photoinduced addition followed by an intramolecular 5‐ exo‐tet anionic substitution after insertion.
Language: Английский
Citations
11
Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110900 - 110900
Published: Jan. 1, 2025
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(20), P. 13232 - 13244
Published: Sept. 28, 2023
Molecules with precise sultine structures are particularly sought after since the function of a molecule depends on this interesting structure. Despite positive pivotal significance sultines in synthesis, medicine, and materials science, sultines' chemistry long remains unexplored due to their inaccessibility; only very limited protocols have been developed. Here, we report an energy-transfer-powered intramolecular radical–radical cross-coupling cyclization for practical atom-economical assembly otherwise challenging-to-access under mild operationally simple conditions using inexpensive organic photocatalyst. Importantly, work presents method trifluoromethyl radical generation from alkyl trifluoromethanesulfinate, obtained were confirmed as promising electrolyte additives high-voltage lithium batteries employing LiNi0.5Mn1.5O4 cathodes carbonate electrolytes. Sultines applied build highly valuable sultones, mercaptoalkanols, disulfides. Mechanistic studies density functional theory calculations supported that reaction likely proceeds through process.
Language: Английский
Citations
9
Acta Chimica Sinica, Journal Year: 2024, Volume and Issue: 82(2), P. 171 - 171
Published: Jan. 1, 2024
Language: Английский
Citations
2
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 6, 2024
A multicomponent heterogeneous semiconductor photocatalytic sulfinylsulfonylation of alkenes with alkyl iodides and SO
Language: Английский
Citations
2
Synlett, Journal Year: 2024, Volume and Issue: 35(10), P. 1180 - 1184
Published: Jan. 2, 2024
Abstract The development of an oxa-Diels–Alder reaction between sultines and carbonyl compounds is reported. o-Quinodimethanes, generated from sultines, undergo a [4+2]-cycloaddition with activated aldehydes or ketones in the presence Cu(OTf)2 to provide variety functionalized isochromans, including spiroisochromans, up 99% yield. developed protocol demonstrates broad functional-group compatibility tolerates unprotected isatins bearing free NH-functionalities.
Language: Английский
Citations
1
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
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3881 - 3893
Published: Jan. 1, 2024
We have successfully developed a versatile approach for synthesizing sulfinimidate esters, by making use of thiols, amines, and alcohols.
Language: Английский
Citations
1
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown
Published: July 14, 2024
A visible-light-initiated energy-transfer enabled radical cyclization for the divergent synthesis of polycyclic γ-sultine derivatives has been developed. The reaction provides an alternative and expeditious access to benzofused frameworks, analogues γ-lactones γ-sultones, features good functional group compatibility, mild conditions excellent diastereoselectivity. robustness application potential this method have also successfully displayed by two gram-scale reactions sultones. Mechanistic studies indicated transformations through a possible intramolecular homolytic substitution or hydrogen atom transfer process mainly.
Language: Английский
Citations
1