SusChEM: RUI: Organohypervalent Iodine Chemistry

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Viktor V. Zhdankin of the Department of Chemistry and Biochemistry at University of Minnesota Duluth will explore the chemistry of trivalent and pentavalent iodine compounds, which are efficient and environmentally benign oxidizing reagents with numerous applications in organic synthesis. While organohypervalent iodine compounds are well-established stoichiometric reagents, little progress has been made in the development of new catalytic reactions promoted by hypervalent iodine. Studies of new, metal-free catalytic reactions based on hypervalent iodine chemistry and an exploratory search for new and potentially useful organohypervalent iodine compounds are proposed. Synthetically useful methodologies based on the new, iodoarene-catalyzed oxidative transformations, such as the Hofmann rearrangement of amides to amines and the oxidative heterocyclization reactions leading to isoxazole derivatives and N-substituted indoles, will be investigated. Organoiodine-catalyzed enantioselective aziridination reactions on the basis of a recently discovered metal-free catalytic procedure for the aziridination of alkenes using organic iodide as catalyst will also be studied. An exploratory study on the preparation, structural characterization, and chemical properties of new, potentially useful hypervalent iodine amides, imides, and ylides will be also performed.New synthetic methodology based on organohypervalent iodine 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 this methodology will have an impact on any area of activity in which the synthesis of molecules is needed, such as the pharmaceutical, chemical, agricultural industry, and the biological and chemical research activities. In addition, this project will provide excellent training of students, from pre-undergraduate to post-doctoral, including those from groups historically underrepresented in the sciences.