Ring-opening/1,3-difunctionalization of Cyclopropanes Enabled by Copper Catalysis and Electrochemistry

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With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Qiu Wang of Duke University is studying the chemistry of cyclopropanes to explore their potential in organic synthesis. This project will develop new catalytic methods that can transform readily available cyclopropanes into high value-added, richly functionalized products of value as molecular building blocks for broad use in industry and academia. The proposed research will also provide engaged graduate students with strong training in synthetic methodology, catalysis, and organic synthesis. The educational activities aim to improve the diversity of the science, technology, engineering, and mathematics (STEM) training pipeline, to broaden student participation in research, and to foster outreach activities for local community.Synthetic applications of simple cyclopropanes to deliver versatile functionalized products without the necessity for specific activating substituents are highly attractive, yet represent unmet challenges. This application aims to develop new activation strategies and novel methods to achieve selective ring-opening/1,3-difunctionalization reactions of non-activated cyclopropanes. To achieve this goal, Dr. Wang and her team will investigate copper-catalysis, electrolysis, and photocatalysis to promote selective C–C cleavage of cyclopropanes to achieve rapid access to diverse 1,3-difunctionalized motifs and heterocyclic frameworks that are highly sought-after in organic synthesis, medicinal chemistry, and agrochemistry. In the longer term, insights obtained from this project will likely facilitate the invention and development of new multi-component reactions related to copper catalysis, electrocatalysis, radical chemistry, and heterocyclic chemistry.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.