Tetrahedron, Год журнала: 2023, Номер 151, С. 133815 - 133815
Опубликована: Дек. 28, 2023
Язык: Английский
Chemistry - A European Journal, Год журнала: 2024, Номер 30(43)
Опубликована: Июнь 4, 2024
Vinyl sulfones are crucial building blocks in synthetic chemistry and core structural units of pharmaceutically active molecules, thus extensive investigations have been conducted on the construction these skeletons. In contrast to classical approaches, radical sulfonylation alkynes for producing vinyl has garnered considerable interest because its mild conditions high efficiency. Radical sulfonation typically begins with sulfonyl attacking alkynes, followed by further functionalization. Moreover, association metal-catalyst-free systems multicomponent reactions (MCRs) offers an environmentally friendly pathway efficiently constructing complex scaffolds from readily available partners. However, there is no comprehensive review summarizing advancements alkynes. Hence, we provide a categorical overview based objects (hydrosulfonylation, carbosulfonylation, aminosulfonylation, oxysulfonylation, sulfosulfonylation, selenosulfonylation, iodosulfonylation), along interpretations reaction mechanisms.
Язык: Английский
Процитировано
6
Molecules, Год журнала: 2024, Номер 29(4), С. 782 - 782
Опубликована: Фев. 8, 2024
We present the first example of visible-light-mediated multicomponent annulation 1,7-diynes by taking advantage quadruple cleavage olf carbon-halogen bonds BrCCl3 to generate a C1 synthon, which was adeptly applied preparation skeletally diverse 3-benzoyl-quinolin-2(1H)-one acetates in moderate good yields. Controlled experiments demonstrated that H2O acted as both oxygen and hydrogen sources, gem-dichlorovinyl carbonyl compound exhibited critical intermediate this process. The mechanistic pathway involves Kharasch-type addition/6-exo-dig cyclization/1,5-(SN”)-substitution/elimination/binucleophilic 1,6-addition/proton transfer/tautomerization sequence.
Язык: Английский
Процитировано
5
Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
An electrochemical redox C(sp3)-H arylsulfonylation of xanthenes has been developed using aryl diazonium tetrafluoroborates and DABSO as the arylsulfone source. This radical reaction proceeds via formation arylsulfonyl radicals from between DABSO, followed by a cross-coupling process. Notably, occurs in absence any catalyst or external oxidant, providing efficient sulfonylation with broad functional group compatibility.
Язык: Английский
Процитировано
0
Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown
Опубликована: Май 1, 2025
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11874 - 11884
Опубликована: Авг. 3, 2023
A direct arylsulfonylation of β,γ-unsaturated hydrazones method, in which sulfonated pyrazolines are accessed by a three-component reaction hydrazones, DABSO, and aryldiazonium tetrafluoroborates, has been developed without external oxidants or catalysts. This transformation is triggered the formation arylsulfonyl radicals situ from tetrafluoroborates enabled controllable generation C center radical, DABSO was utilized as sulfone source an oxidant this radical-mediated cascaded reaction. wide range substrates can be applied process to afford good yield, it amenable for gram-scale synthesis.
Язык: Английский
Процитировано
7
Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Дек. 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.
Язык: Английский
Процитировано
2
Molecules, Год журнала: 2023, Номер 28(17), С. 6356 - 6356
Опубликована: Авг. 30, 2023
In this mini-review, we present our concepts for designing multicomponent reactions with reference to a series of sequential radical that have developed. Radical are well suited the design due their high functional group tolerance and low solvent sensitivity. We focused on photolysis interelement compounds heteroatom–heteroatom single bond, which readily generates heteroatom-centered radicals, studied photoinduced addition unsaturated compounds. First, background is described, basic methodology construction explained. Next, examples involving two one compound presented, as Furthermore, intramolecular cyclization processes described.
Язык: Английский
Процитировано
5
Synlett, Год журнала: 2024, Номер unknown
Опубликована: Апрель 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
Язык: Английский
Процитировано
1
Tetrahedron, Год журнала: 2024, Номер 153, С. 133855 - 133855
Опубликована: Янв. 26, 2024
Язык: Английский
Процитировано
0
Synthesis, Год журнала: 2024, Номер 57(02), С. 275 - 295
Опубликована: Авг. 28, 2024
Abstract The utilization of sulfur heterocycles in organic synthesis has attracted significant attention due to their wide-ranging applications. This review showcases the syntheses diverse embedded with amino acid derivatives, polycycles, spirocycles, cyclophanes, and other complex scaffolds. reported methods extend beyond compound highlight use different reagents for constructing heterocycles. Review also discusses utility a variety sulfur-containing starting materials generation target molecules. 1 Introduction 2 Potassium Thioacetate 3 Thiazolidine-2,4-dione 4 Rhodanines 5 Sodium Sulfide 6 Thiotetronic Acid 7 Thiadiazoles 8 Thiophene 9 Rongalite 10 Sulfur Dioxide 11 Divinyl Sulfone 12 Heterocycles Based on Boronic Acids 13 Miscellaneous 14 Summary
Язык: Английский
Процитировано
0