Synthesis of Sulfonium Ylides from β-Diketones
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Authors
Filius, Sadie
Date of Issue
2025-04-25
Type
Presentation
Language
en_US
Subject Keywords
Other Titles
Abstract
Sulfonium ylides are desirable precursor molecules for the photochemically induced generation of carbene intermediates. Carbenes are highly reactive organic molecules in which a carbon atom is bonded to two atoms with one lone pair of electrons. A frequent synthetic use of carbenes is in the synthesis of new carbon-carbon bonds, a key process in pharmaceutical development. Additionally, carbenes are highly abundant in interstellar space, making them important in foundational research, which can deepen understanding of reactivity and potential applications. In this work we sought an efficient and economical synthesis of sulfonium ylide precursor compounds. Traditionally sulfonium ylides have been synthesized from diazo compounds, but rarely directly from β-diketones. By using β-diketones as starting material, the need for diazo compounds in the synthetic pathway can be eliminated, reducing a two-step synthesis to a one-step process. Varying reaction conditions were explored in an attempt to maximize the efficiency of the proposed one step synthetic pathway.