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

Catalyst‐Free Direct Hydrocarbonation of Terminal Alkynes Toward E‐Alkene Substituted Stabilized Sulfoxonium Ylides DOI

Haiting Wu,

Yougen Xu,

Lin An

et al.

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

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

Light-induced β-hydroxy sulfone synthesis in DNA-encoded libraries DOI

Lijun Xue,

Jiaqing Yu,

Ying Zhong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(54), P. 6885 - 6888

Published: Jan. 1, 2024

We here describe a visible-light photooxidation of sulfinate salts with common alkenes to yield β-hydroxy sulfones on DNA. This process demonstrates broad substrate compatibility and achieves conversion rates ranging from moderate excellent. Most importantly, it presents straightforward, efficient, metal-free approach for synthesizing Csp

Language: Английский

Citations

Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst DOI

Jingwen Wei, Thong Van Pham, Emmanuel Ifeanyi Attah

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 21, 2024

The one-step synthesis of tetra-substituted benzenes was accomplished via gold-catalyzed diyne-ene annulation. Distinguished from prior modification methods, this novel strategy undergoes formal [3+3] cyclization, producing polysubstituted with exceptional efficiency. critical factor enabling transformation the introduction amides, which were reported for first time in gold catalysis as covalent nucleophilic co-catalysts. This interesting protocol not only offers a new to achieve functional high efficiency, but also enlightens potential reaction pathways within alkyne activation processes.

Language: Английский

Citations

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

Recent approaches for the synthesis of heterocycles from amidines via metal catalyzed C-H functionalization reaction DOI

Youpeng Zuo,

Pengfei Zuo,

Meijun Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5014 - 5031

Published: Jan. 1, 2024

Transition metal catalyzed C-H bond activation has become one of the most important tools for constructing new chemical bonds. Introducing directing groups to substrates is key a successful reaction, these can also be further transformed in reaction. Amidines with their unique structure and reactivity are ideal transition metal-catalyzed transformations. This review describes major advances mechanistic investigations activation/annulation tandem reactions amidines until early 2024, focusing on unsaturated compounds, such as alkynes, ketone, vinylene carbonate, cyclopropanols derivatives. Meanwhile this manuscript explores reaction different carbene precursors, example diazo azide, triazoles, pyriodotriazoles, sulfoxonium ylides well own activation/cyclization reactions. A bright outlook provided at end manuscript.

Language: Английский

Citations

Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols DOI

Janakiram Vaitla,

Srashti Bhardwaj,

Raju Sen

et al.

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

Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst DOI

Jingwen Wei, Thong Van Pham, Emmanuel Ifeanyi Attah

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(39)

Published: July 8, 2024

Abstract The one‐step synthesis of tetra‐substituted benzenes was accomplished via gold‐catalyzed diyne‐ene annulation. Distinguished from prior modification methods, this novel strategy undergoes formal [3+3] cyclization, producing polysubstituted with exceptional efficiency. critical factor enabling transformation the introduction amides, which were reported for first time in gold catalysis as covalent nucleophilic co‐catalysts. This interesting protocol not only offers a new to achieve functional high efficiency, but also enlightens potential reaction pathways within alkyne activation processes.

Language: Английский

Citations

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