NSF-DFG Echem: CAS: Hydrofunctionalization of Alkenes by non-Redox Paired Electrocatalysis

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With the support of the Chemical Catalysis program in the Division of Chemistry, Song Lin of Cornell University is studying the enantioselective hydrofunctionalization of alkenes by non-redox paired electrocatalysis along with collaborators at Carl von Ossietzky University Oldenburg in Germany. The Lin research group aims to develop electrocatalytic processes for the synthesis of value-added organic compounds. The long-term objective of this research program is to facilitate the development of a generalizable electrocatalytic process or wide impact in synthetic chemistry, with possible application in the stereocontrolled synthesis of building blocks for new pharmaceuticals, agrochemicals, and catalysts. Many of these important compounds contain carbon-halogen and carbon-carbon bonds. The goal of this research is to establish efficient, selective, and sustainable reaction technologies that will promote the formation of carbon-halogen and carbon-carbon bonds using abundant feedstock chemicals. Electrochemistry—a process that directly uses electricity to drive chemical reactions—is an intrinsically efficient, selective, and sustainable technology. The introduction of catalysis can further augment the energy efficiency of electrochemical reactions and offer opportunities to 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. In addition to contributing to the advancement of scientific knowledge and improving fine chemical manufacturing, the project will also exert broader impacts on the training of students through research and international collaboration with the German team. The project is being funded through the "NSF-DFG Lead Agency Activity in Electrosynthesis and Electrocatalysis (NSF-DFG EChem)" opportunity, a collaborative solicitation that involves NSF and Deutsche Forschungsgemeinschaft (DFG).Together with collaborators at Carl von Ossietzky University Oldenburg in Germany, Song Lin of Cornell University is developing electrocatalytic methods for the hydrofunctionalization of alkenes. The proposed research will enlist the combination of paired electrolysis with redox-active metal catalysis to enable the generation of dual catalytic intermediates to achieve the desired hydrofunctionalization reactions. Two objectives will be pursued simultaneously, including (i) establishing non-redox paired electrocatalysis in the context of hydrochlorination and (ii) mechanistic investigation of non-redox paired electrocatalysis using electroanalytical and spectroscopic tools. Upon obtaining initial proof of principle, the new catalytic strategy will be further expanded to other types of hydrofunctionalization reactions beyond hydrochlorination. Finally, the Lin team will develop an electrochemical short course that aims to educate organic chemists with little electrochemistry experience and provide them with the knowledge and guidance needed to set up their own electrolysis experiments.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.