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
Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 8992 - 8996
Published: Dec. 12, 2023
Herein, we report the divergent benzannulation for highly substituted arenes using vinyl sulfoxonium ylides and ynones. The addition of ynone at γ-position leads to dienyl ylide that can undergo selective annulation under different conditions give m-terphenyls parabens. Moreover, control experiments quantum chemical calculations reveal two distinct reaction mechanisms both annulations.
Language: Английский
Citations
11
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(28), P. 3846 - 3849
Published: Jan. 1, 2024
The coupling of ylide-derived carbene with diazo-derived generated dienoates via cascade catalysis. Similarly, the reaction oxocarbenium ion afforded alkylidenebutenolide synergistic
Language: Английский
Citations
4
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 28, 2025
Here, we describe the synthesis of novel α-carbonyl-α'-vinyl sulfoxonium ylides under ambient, catalyst-free, and additive-free conditions, demonstrating broad substrate scope scalability using β-ketosulfoxonium α-ynone-esters. Furthermore, these serve as versatile intermediates for highly substituted furans via Brønsted acid (p-TsOH) catalysis at 130 °C. This approach offers key advantages, including wide compatibility, divergent product formation from common precursors, gram-scale feasibility, good to excellent yields.
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
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
Citations
0