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

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 and scalability using β-ketosulfoxonium ylides and α-ynone-esters. Furthermore, these ylides serve as versatile intermediates for the synthesis of highly substituted furans via Brønsted acid (<i>p</i>-TsOH) catalysis at 130 °C. This approach offers key advantages, including wide substrate compatibility, divergent product formation from common precursors, gram-scale feasibility, and good to excellent yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-29
DOI
https://doi.org/10.1021/acs.joc.5c00245
Citations
1
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.94

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article

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

Ravindar Kontham, Balasaheb R. Borade, Gamidi Rama Krishna, Sudhir Rama Ingale et al.
1 citations
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
0.94
article

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

Ravindar Kontham, Balasaheb R. Borade, Gamidi Rama Krishna, Sudhir Rama Ingale, Manas Ranjan Sahu
article en
1 citations

Abstract

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 and scalability using β-ketosulfoxonium ylides and α-ynone-esters. Furthermore, these ylides serve as versatile intermediates for the synthesis of highly substituted furans via Brønsted acid (<i>p</i>-TsOH) catalysis at 130 °C. This approach offers key advantages, including wide substrate compatibility, divergent product formation from common precursors, gram-scale feasibility, and good to excellent yields.

The Journal of Organic ChemistryVol. 90(18)
National Chemical Laboratory (IN), Academy of Scientific and Innovative Research (IN)
Council of Scientific and Industrial Research, India, University Grants Commission
Openalex Percentile: Top 27%
Catalytic Alkyne Reactions
0.94
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Divergent Access to α-Carbonyl-α′-vinyl Sulfoxonium Ylides and Polysubstituted Furans from β-Ketosulfoxonium Ylides and Ynone-Esters — Ravindar Kontham, Balasaheb R. Borade, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS