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 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

Divergent Access to α-Carbonyl-α′-vinyl Sulfoxonium Ylides and Polysubstituted Furans from β-Ketosulfoxonium Ylides and Ynone-Esters DOI

Sudhir Rama Ingale,

Manas Ranjan Sahu,

Balasaheb R. Borade

et al.

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

Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts DOI

Ramesh Kumar Vishwakarma,

Raju Sen,

Shalu Deshwal

et al.

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

Diastereoselective Cyclopropanation of α,β- Unsaturated Carbonyl Compounds with Vinyl Sulfoxonium Ylides DOI

Shalu Deshwal,

Dinesh Kumar Gopalakrishnan,

Alok Purohit

et al.

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

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

Citations

0