CAS: Synthetic and Mechanistic Studies of Nickel-Catalyzed 1,2-Dicarbofunctionalization of Alkenes

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With the support of the Chemical Synthesis and Chemical Catalysis Programs in the Division of Chemistry, Professor Keary Engle of The Scripps Research Institute and Professor Peng Liu of the University of Pittsburgh are studying the development of new chemical reactions to streamline the production of valuable compounds, including medicinally relevant compounds, agrochemicals, and functional materials. The reactions that are being studied simultaneously connect three widely available feedstock chemicals using earth abundant nickel catalysts. This collaborative project is combining insights from experiment, computation, and machine learning to identify optimal nickel catalysts that attach alkenes (feedstock molecules that contain a carbon–carbon double bond (C=C) bond) to two additional building blocks to rapidly build molecular complexity. Professor Engle, Professor Liu and their research teams are also leading synergistic outreach activities to promote engagement with STEM disciplines among diverse populations. These efforts include developing virtual reality technology to teach chemical concepts in the classroom and in the local community, creating open-access online databases and short courses to share know-how in computational organic chemistry, and involving undergraduate and high school interns from historically underrepresented groups in collaborative research experiences. These activities that bridge the Chemical Synthesis and Chemical Catalysis programs are helping to improve the sustainability and innovation of the chemical industry while advancing the technical workforce of the United States.Multicomponent reactions promoted by base metal catalysts are important processes that combine the advantages of efficiency and sustainability. Professor Engle and Professor Liu are developing nickel-catalyzed, three-component, cross-coupling reactions to unite alkenes, organohalides, and organometallic reagents. The products of these transformations are structurally complex, contain one or more stereocenters, and naturally map onto to chemical substructures that are useful in academia and industry. This collaborative research project leverages the combined expertise of the Engle lab in experimental organometallic chemistry and the Liu lab in computational organic chemistry to study reaction mechanisms, design chiral ligands for asymmetric induction, and predict catalyst physical properties from in silico descriptors. These activities are providing cutting-edge interdisciplinary training for a diverse group of graduate, undergraduate, and high school students who are learning from two PIs and engaging with two research groups at two institutions.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.