SuSChEM: GOALI: Enabling Photoredox Catalysis in the Industrial Setting

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The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Gary Molander. Professor Molander is a faculty member in the Department of Chemistry at the University of Pennsylvania. He has developed a new way of making carbon-carbon bonds. The research is of broad scientific impact since carbon-carbon bonds are used in chemicals produced by the pharmaceutical, agrochemical, fine chemical, materials, and commodity chemical (e.g., display devices, cosmetics, etc.) industries. Using this new method for making carbon-carbon bonds, the Molander group is working toward more sustainable approaches to the construction of complex molecules. Central to this method is the fact that the reactions are driven by visible light, require no heating of the chemical reaction. The reactions can also be conducted in the absence expensive, precious metals. The simple reaction conditions make the method not only more sustainable, but also more economically viable. This potential has attracted the chemical company, Novartis as a partner. Working together, Novartis and the Molander group are developing industrial applications of the new reaction methods. The project lies at the interface of organic and inorganic chemistry. With insight into industrial research provided by the project, students gain for important perspectives on the industrial job market. Outreach activities involving both academic and industrial partners in the project are targeting underrepresented groups. Photoredox/nickel dual catalysis provides a means to form new carbon-carbon bonds in new ways. This paradigm, combined with carbon-hydrogen (C-H) functionalization, provides a powerful combination for the sustainable synthesis of complex organic molecules. In the research, the following lines of inquiry are pursued: 1. Can conditions be found wherein acyl and alkyl radicals can be generated through visible light photocatalysis and engaged in nickel-catalyzed cross-coupling reactions? 2. Can intramolecular hydrogen atom transfer be controlled in a manner that allows arylation at specific sites along an alkyl chain? 3. Can the specificity be changed through polarity reversal by adding amine-boranes or NHC-boranes to the reaction mixture? 4. Can these new synthetic methods be translated to large scale synthesis using photoflow techniques with partners at Novartis? This last aspect provides outreach possibilities and translation of basic science to the industrial setting.