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Publication Date
2022-05-09
First Advisor
Alexandra E. Strom
Document Type
Honors Project
Degree Name
Bachelor of Arts
Department
Biochemistry
Keywords
reaction optimization, preliminary investigation of substrate scopes and mechanistic studies of a novel iron-catalyzed oxidative ๐ผ-amination reaction to couple carbonyl derivatives with primary sulfonamides and other nitrogen sources
Abstract
๐ผ-Amination of carbonyl derivatives has been a key area of research due to the importance of ๐ผ-amino carbonyls in pharmaceutical and biologically active compounds. It has been achieved via both metal-mediated and metal-free catalysis, which has been reported by multiple laboratories. However, current methods mostly involve the formation of ๐ผ-halogenated ketone or enolates, or they often depend on electrophilic nitrogen sources. And despite their geological abundance and low monetary and environmental costs, first-row transition metals such as iron have not been fully developed in terms of their role in facilitating ๐ผ-amination. This research is focused on the development of iron-catalyzed ๐ผ-amination under oxidative conditions. Primary sulfonamides and other nitrogen sources were coupled to the ๐ผ-position of the deoxybenzoin carbonyl without prior functionalization of either coupling partner. Current research is focused on testing the scope of the reaction using ketones and sulfonamides either commercially available or synthesized in the laboratory and studying the reaction mechanism.
Rights
ยฉ2022 Fubin Song. Access limited to the Smith College community and other researchers while on campus. Smith College community members also may access from off-campus using a Smith College log-in. Other off-campus researchers may request a copy through Interlibrary Loan for personal use.
Language
English
Recommended Citation
Song, Fubin, "Development of an Iron-catalyzed Oxidative ๐ผ-Amination Method to Couple Carbonyl Derivatives with Primary Sulfonamides and Other Nitrogen Sources" (2022). Honors Project, Smith College, Northampton, MA.
https://scholarworks.smith.edu/theses/2492
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