Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides DOI

Siru Feng,

Hailong Zhang, Jinhua Liu

et al.

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

Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones DOI

Shalu Deshwal,

Daksh Singh Davas,

Srashti Bhardwaj

et al.

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

Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates DOI Creative Commons

Daksh Singh Davas,

Dinesh Kumar Gopalakrishnan,

Sandeep Kumar

et al.

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

Stereoselective Three-Component Carbocyclization of 1,7-Enynes with Sulfoxonium Ylides and Water under Photoredox Catalysis DOI

Ning Xian,

Jiang Yin,

Xiaochen Ji

et al.

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

Stereoselective gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols via Metalloradical Catalysis DOI

Srashti Bhardwaj,

Dinesh Kumar Gopalakrishnan,

Shalu Deshwal

et al.

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

Divergent Approach to Highly Substituted Arenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Ynones DOI

Daksh Singh Davas,

Dinesh Kumar Gopalakrishnan,

Krishnendu Bar

et al.

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

Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals DOI

Dinesh Kumar Gopalakrishnan,

Srashti Bhardwaj,

Sandeep Kumar

et al.

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

Synthesis and Applications of π-Conjugation-Extended Vinyl Sulfoxonium Ylides DOI
Sandeep Kumar,

Daksh Singh Davas,

Krishnendu Bar

et al.

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

High-throughput experimentation and machine learning-promoted synthesis of α-phosphoryloxy ketones via Ru-catalyzed P(O)O-H insertion reactions of sulfoxonium ylides DOI
Lin An, Jingyuan Liu,

Yougen Xu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Language: Английский

Citations

3

Perhaloacylation of α-Carbonyl Sulfoxonium Ylides DOI
Varun Anand, Namrata Rastogi

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

Ylide-Induced Ring Contraction of Coumarins to Benzofurans: Applications to the Synthesis of Bis-Heterocycles DOI
Sandeep Kumar,

Dinesh Kumar Gopalakrishnan,

Shashank Shrotriya

et al.

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