A New Class of Selenium Catalysts for the Amination of Alkenes and Alkynes

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A New Class of Selenium Catalysts for the Amination of Alkenes and AlkynesMost organic molecules in biology contain nitrogen atoms that are critical to their activity. In making these compounds, chemists employ many powerful catalysts based on transition metals. As we progress towards a greener, more sustainable future, it is critical that we find new catalysts that are equally powerful, yet less expensive and less toxic. In this project, Prof. Michael of the Department of Chemistry at the University of Washington is studying catalysts based on selenium as alternatives to transition metal-based catalysts. These catalysts can introduce nitrogen-containing groups at specific, key points in simple organic molecules. This project is determining how changes to the structure of the selenium catalysts controls these reactions. Prof. Michael is engaged in outreach activities that provide research and learning opportunities to highly gifted and talented young scientists through his work with the Center for Excellence in Education and the Research Science Institute and Research Science Initiative, where he teaches high school students in the US and China about cutting-edge research in chemistry.With funding from the Chemical Catalysis Program of the Chemistry Division, Prof. Michael of the University of Washington is studying how ligands normally used for transition metal catalysts, such as phosphines and N-heterocyclic carbenes, can be employed to control the catalytic reactivity of selenium. These reactions will allow the transformation of inexpensive hydrocarbon starting materials into more complex compounds by the selective introduction of nitrogen substituents via allylic, vinylic and propargylic C-H amination reactions, as well as diamination and hydroamination reactions. The fundamental reaction mechanisms and key intermediates in these transformations are being studied by testing structure-function relationships and examining intermediates by multi-nuclear (1H, 31P, 77Se) NMR spectroscopy. Prof. Michael is engaged in outreach activities that mentor highly gifted and talented young scientists through his work with the Center for Excellence in Education and the Research Science Institute and Research Science Initiative.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.