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.
Authors
- Ravindar Kontham (ORCID: https://orcid.org/0000-0002-5837-2777)
- Balasaheb R. Borade (ORCID: https://orcid.org/0000-0002-2585-3216)
- Gamidi Rama Krishna (ORCID: https://orcid.org/0000-0001-5313-7746)
- Sudhir Rama Ingale
- Manas Ranjan Sahu
Institutions
- National Chemical Laboratory (IN)
- Academy of Scientific and Innovative Research (IN)
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
Funders
- Council of Scientific and Industrial Research, India
- University Grants Commission