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

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

0

Silver-Catalyzed Doyle–Kirmse Reaction of Allyl Sulfides with Vinyl Triftosylhydrazones DOI
Ziying Li, Zhaohong Liu, Paramasivam Sivaguru

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated in situ from triftosylhydrazones the presence silver catalyst. This protocol features mild conditions, exhibits broad substrate scope exceptional functional group tolerance, provides corresponding 1,5-dienyl 1,4-enallenyl high yields. Moreover, gram-scale synthesis, late-stage modifications complex molecules, post-synthetic transformations were performed to demonstrate applicability this protocol.

Language: Английский

Citations

0

Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex DOI

Xiaoting Xie,

Zhifei Zhao,

Jun Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 17, 2024

A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach assembling 1,2,3-trisubstituted chiral cyclopropane alkyl structural units, which had advantages such as wide range substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments transformation cycloaddition products were carried out to highlight practicality method.

Language: Английский

Citations

2

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

0

Nickel-Catalyzed Multicomponent Assembly of Alkynes toward α-CF3-Alkenes DOI
Ling Li,

Yingmei Li,

Chongchong Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5566 - 5570

Published: June 21, 2024

We disclose an efficient nickel catalytic system for expediting the coupling of alkynes with fluoroalkyl hydrazones and boronic acids, thus facilitating synthesis stereospecific α-fluoroalkyl-alkene derivatives. 3H-Pyrazoles might be involved as key intermediates through a nitrogen-releasing process, enabling subsequent acids to afford 1,2-difunctional alkenes in highly step-economical fashion. This tandem platform demonstrates broad functional group tolerance, including complex natural products drug-like molecules.

Language: Английский

Citations

0

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