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

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
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