RUI: Development of New Reagents and Synthetic Methodologies Based on Hypervalent Iodine Chemistry

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With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Viktor V. Zhdankin of the University of Minnesota Duluth (UMD) is studying the development of new reagents and synthetic methodologies based on the organic chemistry of iodine. The project is exploring the preparation and fundamental chemistry of new hypervalent iodine compounds. The ability of hypervalent iodine species to modify organic compounds when coupled with their efficiency and sustainability makes them useful among academic and industrial scientists. This utility is the result of iodine behaving much like a transition metal in many applications. The continued exploration and utilization of these similarities is leading to the development of new useful methodologies for modern organic chemistry. More broadly speaking, this project is at the interface of organic and inorganic chemistry and is well-suited for undergraduate, graduate, and more advanced researchers including researchers in industry. The project is expected to provide high level of education and training for students, many of whom are underrepresented in science. A broad study of new, metal-free, iodine-mediated reactions and an exploratory search for new and potentially useful hypervalent reagents is proposed. Specific objectives include: (i) the development of pseudocyclic arylbenziodoxaboroles as benzyne precursors and highly efficient electrophilic arylating reagents under neutral, aqueous conditions, (ii) the exploration of 4-iodonium substituted arylboronic acids as para-benzyne precursors, (iii) the study of the synthesis and reactivity of stabilized iodonium derivatives of porphyrins and dipyrromethenes, and (iv) the search for new types of polyvalent iodine compounds that are stabilized by internal halogen bonding. New synthetic methodologies based on these efforts will contribute to the discovery of environmentally benign methods for chemical synthesis as they utilize non-toxic iodine compounds in water as catalysts or as recoverable/recyclable reagents. The successful development of this methodology will have an impact on the areas of science where the synthesis of organic molecules is required, such as in academia and in the pharmaceutical, chemical, and agricultural industries.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.