The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 25, 2024
Carbene-catalyzed [3 + 3] annulation of enals and vinyl sulfoxonium ylides has been demonstrated. This method efficiently synthesizes a range 2-sulfenylidene-3-cyclohexen-1-ones with high atom economy. Notably, the presence ylide moiety in obtained products significantly enhances their potential for further synthetic transformations.
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 809 - 813
Published: Jan. 23, 2024
Herein, we report the synthesis of 2H-chromenes via catalyst-controlled highly regioselective [3 + 3] annulation vinyl sulfoxonium ylides with quinones. Under boron-catalyzed conditions, reaction between ylide and quinone resulted in formation 2H-chromene-4-carboxylates. In contrast, a different mechanistic pathway was observed when utilizing Ru(II) catalytic system, which led to 2H-chromene-2-carboxylates through furan intermediate.
Language: Английский
Citations
12
JACS Au, Journal Year: 2024, Volume and Issue: 4(3), P. 1073 - 1080
Published: March 1, 2024
Herein, we report a highly regioselective [4 + 2]-annulation of vinyl sulfoxonium ylides with ynoates under light-mediated conditions. The reaction proceeds through the new dienyl ylide, which undergoes photolysis blue light irradiation to give substituted naphthalene scaffolds. method presented here operates at room temperature and does not require addition an external photosensitizer. in situ-generated ylide absorbs acts as photosensitizer for formation arenes. synthetic potential these benzannulations was further illustrated by various transformations scale-up reaction. Moreover, control experiments quantum chemical calculations reveal mechanistic details developed
Language: Английский
Citations
9
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2805 - 2815
Published: Feb. 8, 2024
Multicomponent reactions that involve carbenes with nucleophiles and electrophiles have demonstrated broad applications in synthetic chemistry. However, because of the high reactivity transient carbenes, involving two carbene precursors nucleophile presence a metal catalyst remain unexplored. Herein, three-component stereoselective gem-difunctionalization diazo compounds thiols vinyl sulfoxonium ylide is disclosed via Co(II)-based metalloradical catalysis. The key aspect present strategy to exploit intrinsic difference ylides thiol catalysts. Doyle–Kirmse rearrangement sulfonium involves convergent assembly situ-generated intermediates, such as allyl sulfide α- metalloalkyl radical complex, provide expeditious access tertiary scaffolds. Combined experimental quantum chemical calculations unveil intricate mechanism this reaction. Furthermore, theoretical studies on noncovalent interactions selectivity-determining transition states explain origin experimentally obtained diastereoselectivity.
Language: Английский
Citations
6
ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(6)
Published: Feb. 1, 2025
Abstract Benzannulation is one of the most important methods to construct simplest aromatic ring, i.e., benzene ring. Various efforts synthesize derivatives were already made, but they generally require some transition metal species in stoichiometric or catalytic amounts carry out this transformation which contaminates with metal‐based impurity. On other hand, reactant, alkyne used for these transformations also quite expensive nature. Keeping facts mind, a series 2,4,6‐trisubstituted benzophenones (vis‐à‐vis 1,2,4,6‐tetrasubstituted benzenes) synthesized under and solvent free conditions using simple chemicals arylmethyl ketones, aldehydes, sodium hydride. The beauty methodology that 4 6 σ all 3 π bonds ring generated within reaction vessel. Using methodology, bearing heterocyclic groups can be readily accessed.
Language: Английский
Citations
0
Advanced Science, Journal Year: 2025, Volume and Issue: unknown
Published: April 2, 2025
Amide and alkene moieties are frequently found in natural products privileged structures pharmaceuticals agrochemicals. Moreover, vinyl sulfoxonium ylide can be converted into a broad range of high-value compounds, thus they have been widely employed organic synthesis. However, the synthesis alkene-substituted amide-sulfoxonium ylides via intermolecular hydrocarbonation alkynes remains underexplored. This study describes development high-throughput approach to provide diverse functionalized E-alkene substituted (hetero)amide-sulfoxonium ylides. The reaction occurs under mild metal-free conditions, employing as highly effective nucleophiles, which participate Michael addition reactions with various alkynes, such esters, thioesters, ketones, amides, sulfones. low-cost, operationally simple has substrate scope, high functional group compatibility, excellent regio- stereoselectivity, making it suitable for transformation structurally complex molecules. Furthermore, obtained stabilized directly useful valuable 1,5-dicarbonyl thiabenzene 1-oxide compounds.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 2, 2024
A convenient and practical method has been developed for synthesizing various N-aryl pyrazoles from vinyl sulfoxonium ylides diazonium salts. When using 1,3-disubstituted ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On other hand, employing 2,3-disubstituted results in formation of 1,3,4-trisubstituted The proceeds through novel aryl diazene-derived ylide. Furthermore, this efficiently produces aniline derivatives a one-pot transformation. takes place under transition metal-free, mild conditions easily accessible starting materials, making it approach generating pharmaceutical chemistry.
Language: Английский
Citations
2
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6294 - 6307
Published: Jan. 1, 2024
Vinyl cyclopropane scaffolds were synthesized via a proline-catalysed multicomponent reaction involving vinyl sulfoxonium ylides, aldehydes, and indane 1,3-dione.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 5, 2024
A highly efficient method has been developed for synthesizing 4-dienyl dihydropyridines through the nucleophilic dearomatization of activated pyridines using vinyl sulfoxonium ylides. This reaction follows sequence involving ylide addition to pyridine, [2,3]-sigmatropic rearrangement, and subsequent sulfenic acid elimination. The resulting are then used in synthesis substituted bis-heterocyles. Control experiments quantum chemical calculations were conducted elucidate selectivity mechanistic pathway.
Language: Английский
Citations
1
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2780 - 2785
Published: Jan. 1, 2024
An unprecedented multi-component reaction with solvent participation and a novel conversion of sulfur ylides was developed via Ugi/olefination to construct pyrrolidin-5-one-2-carboxamides.
Language: Английский
Citations
0
Synthesis, Journal Year: 2024, Volume and Issue: unknown
Published: June 21, 2024
Abstract A visible-light-induced multicomponent reaction of vinyl sulfoxonium ylide, thiol, and diazo ester to generate tertiary sulfide is described. The present diastereoselective gem-difunctionalization the can be achieved under mild conditions, as it does not require any additives, catalysts, or transition metals tolerant air moisture. Due more nucleophilicity, ylide undergoes S–H insertion with thiols an allyl intermediate. Simultaneously, photolysis a carbene Subsequently, coupling intermediates generates sulfonium which Doyle–Kirmse rearrangement scaffolds.
Language: Английский
Citations
0