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
Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6736 - 6741
Published: July 29, 2024
A visible-light-induced photoredox three-component carbocyclization reaction of 1,7-enynes with sulfoxonium ylides and water is reported. The protocol provides a facile entry to structurally valuable highly functionalized cyclopenta[c]quinoline scaffolds in chemoselective stereoselective manner. Salient features this method include redox-neutral conditions, no requirement base or other additive, good functional-group tolerance.
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
Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7906 - 7910
Published: Oct. 24, 2023
Herein, we report the synthesis of π-conjugation-extended vinyl sulfoxonium ylides from ylide and electron-deficient alkynes. The new dienoate are used in various transformations, such as X-H (X = S, O) insertion, halogenation, carbene-mediated transformation, radical-mediated reductions to obtain a variety conjugated dienoates.
Language: Английский
Citations
9
Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 10, 2024
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 2, 2025
A mild and efficient protocol for the perhaloacylation of α-carbonyl sulfoxonium ylides has been developed. The commercially available perfluoro- perchloroacid anhydrides were used as acylating agents in catalyst- additive-free reactions to access α-carbonyl-α'-perhaloacyl high yields. reaction offers a simple method prepare valuable polyfluorinated organosulfur molecules.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 15, 2025
We report an unusual ring contraction of 4-chlorocoumarin to benzofuranoyl sulfoxonium ylides using a Corey-ylide. These stabilized were subsequently utilized for the synthesis various valuable bis-heterocycles under both metal and metal-free conditions. The synthetic utility this method is illustrated through known bioactive compounds. Detailed mechanistic investigations quantum chemical calculations have provided insights into mechanism reaction.
Language: Английский
Citations
0