RUI: Hypervalent Iodine Chemistry

This project will continue work on the development of new synthetic methodologies based on the chemistry of hypervalent iodine(III) and iodine(V) compounds, which are efficient and environmentally benign oxidizing reagents with numerous applications in organic synthesis. While hypervalent iodine compounds are well-established reagents, little progress has been made in the development of new catalytic reactions promoted by hypervalent iodine. Studies of new, extremely mild and efficient iodine(V)/transition metal tandem catalytic system for the oxidation of hydrocarbons will be investigated using various aryliodides and transition metals as co-catalysts and Oxone as a stoichiometric oxidant. Several other iodoarene-catalyzed oxidative transformations, such as Hofmann rearrangement of amides to amines, preparation of unsaturated carbonyl compounds from ketones, oxidative cleavage of carbon-carbon double bonds, and the iodine(III)-catalyzed enantioselective oxidations will also be studied. An exploratory search for new and potentially useful hypervalent organic compounds will be also performed. In addition, an important objective of this project is to provide excellent training in advanced chemistry research to BS and MS students and to further strengthen predominantly undergraduate research at University of Minnesota Duluth.

With this award, the Chemical Synthesis program is supporting the research of Professor Viktor V. Zhdankin of the Department of Chemistry and Biochemistry at University of Minnesota Duluth. Professor Zhdankin's research efforts revolve around the development of facile oxidative methods based on hypervalent iodine chemistry. Such chemistry will contribute to environmentally benign methods for chemical synthesis as it utilizes non-toxic compounds of iodine as catalysts or recyclable reagents in aqueous solutions. Successful development of the methodology will have an impact on synthesis in the pharmaceutical industry.