Oxidative Methods for C-C, C-N, and C-O Bond Formation

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With this award, the Chemical Synthesis Program of the Chemistry Division is funding Professor Marisa C. Kozlowski of the Department of Chemistry at the University of Pennsylvania to explore the development of methods for the formation of C-C, C-N, and C-O bonds by facile oxidative reactions. While dimerizations of phenol derivatives are abundant in biological systems, little progress has been made in the development of laboratory methods for the catalytic asymmetric formation of biaryls via oxidative dimerization. Studies to further elucidate the mechanism of this complex catalytic cycle will be undertaken. Higher homologs with interesting material/sensor properties, such as chiral bisnaphthoquinones, bisanthraquinones, and bisphenazines, will be generated using the developed methods and will be studied. The broader impacts involve training undergraduate students, graduate students and postdoctoral researchers, broadening participation through the inclusion of underrepresented populations as researchers on the project, and continuing to build a groundbreaking program in high throughput experimentation that can be utilized routinely in a teaching environment. This work could lead to more efficient methods for the preparation of this class of molecules. Such chemistry will contribute to environmentally benign methods for chemical synthesis as oxygen is used as the terminal oxidizing agent. Successful development of the methodology will have a broad impact as there is an important need for synthetic methods in areas ranging from the pharmaceutical, chemical, materials science, and agricultural industries to basic biological and chemical research endeavors. In addition, this project will provide excellent training of students, from undergraduate to post-doctoral, including those from groups historically underrepresented in the sciences.