Synthetic Methodologies Utilizing Superelectrophiles

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Douglas A. Klumpp of the Department of Chemistry and Biochemistry at Northern Illinois University will explore synthetic chemistry involving highly charged cationic species (superelectrophiles). It has been previously shown that superelectrophiles exhibit large-scale electron delocalization and these charge-charge repulsive effects can be used to drive new types of synthetic reactions. Specific synthetic goals include the preparation of technologically important heterocyclic products, such as indoles, indolizidines, 2-oxyindoles, and aza-steroids. Several natural product syntheses will be explored using this chemistry. Superelectrophilic reactions will also be done to identify synthetic routes to commodity chemicals from biorenewable feedstock.The successful development of the proposed chemistry will improve access to a variety of organic products. These chemical reactions could be valuable to the pharmaceutical, petrochemical, colorants/dye/pigment, and agricultural chemical industries. With both synthetic and mechanistic components, the research will be an ideal training ground for graduate and undergraduate students in chemistry. Moreover, summer research projects are planned for home-schooled, high school age students-typically, high achieving students with little access to formal laboratory sciences.