The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Song Lin. Professor Song Lin is a faculty member in the Department of Chemistry and Chemical Biology at Cornell University. Prof. Lin's lab aims to develop new methods for building organic molecules that contain carbon-nitrogen bonds. Carbon-nitrogen bonds are critically important. Over 85% of the top-selling pharmaceuticals have at least one carbon-nitrogen bond. With this in mind, the goal of the research being pursued is to establish efficient, selective, and sustainable reaction technologies that will promote the formation of carbon-nitrogen bonds from abundant starting materials. Electrochemistry, a process that directly uses electricity to drive chemical reactions, is an intrinsically efficient, selective, and sustainable technology. It would appear to be an ideal method for making carbon-nitrogen bonds in a sustainable manner. However, electrochemical reactions frequently do not afford the chemical selectivity and efficiency necessary to accomplish a particular transformation. The introduction of catalysis that can control the chemical reaction portion of the process can solve this problem. In so doing, the catalyst augments the energy efficiency of electrochemical reactions by offering an opportunity to better control the yield and identity of the end product. The project lies at the interface of organic synthesis, catalysis, and electrochemistry. Therefore, it is also well suited for the education of scientists at all levels. Prof. Lin's group is actively engaged in outreach activities by integrating the key elements of their research into the education and training of the next generation of scientists at both collegiate and K-12 levels.

With funding from the Chemical Synthesis Program of the Chemistry Division, Prof. Lin of Cornell University is developing electrocatalytic methods for new carbon-nitrogen coupling reactions. The proposed research enlists the combination of electrochemistry and redox-active metal catalysis as a general approach to enable highly efficient and chemoselective amination of organic substrates. Three specific aims are being pursued simultaneously. The scope of the electrocatalytic diazidation of alkenes for the synthesis of vicinal diamines is being investigated, the electrochemical azidooxygenation of alkenes for the synthesis of aminoalcohol products is being advanced, and an electrocatalytic paradigm to decarboxylative and deborylative azidations is being expanded. Additional efforts are studying the mechanisms of the electrochemical reactions using kinetic and voltammetric experiments. Finally, the new reaction methods are being employed to improve the synthesis of bioactive complex targets. The proposed educational plan is working to expand the nation's infrastructure for STEM education on collegiate and K-12 levels with a particular emphasis on sustainability. Toward this goal, the Lin Lab is actively participating in the development and promulgation of electrosynthesis-related teaching modules aligned with the Next Generation Science Standards.

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.

National Science Foundation (NSF)
Division of Chemistry (CHE)
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Jin Cha
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Cornell University
United States
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