Novel coupling reactions

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In this project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Patrick J. Walsh at the University of Pennsylvania is developing new reactions that form bonds between two carbon atoms and between a carbon atom and a sulfur atom. Bonds between these elements are found in pharmaceutical compounds, agricultural products, and polymers, and therefore, the proposed research has the potential to impact their corresponding scientific and technological areas. The overarching goal is to develop new catalysts and catalytic processes that are both synthetically useful and practical. Professor Walsh is also studying the reaction mechanisms (i.e., how the reactions work) and the factors that control the chemistry of the catalytic reactions, which will help to optimize the outcomes of the catalysis and to add to our fundamental knowledge base about chemistry. Prof. Walsh is specifically addressing the following catalytic transformations: 1) The arylation of sulfenate anions and the enantioselective synthesis of diarylsulfoxides, which are found in a number of commercialized medications, 2) the development of methods to prepare sulfoximines, including in enantioenriched form, and 3) the introduction of a new class of organocatalysts, sulfenate anions, which have potential applications in a number of C-C bond forming reactions. The broader impacts of this research are in the following areas: 1) The new concepts and synthetic methods introduced herein are expected to have a positive impact on society as they may find application in the preparation of intermediates, medications, agricultural products, or materials in academics or industry, 2) Undergraduate students are gaining experience in chemical research, 3) The PI lectures for high school students about this NSF-supported research 4) The PI disseminates the findings of these investigations by publication and seminars at universities and conferences, and 5) The PI continues an international scientific collaboration outreach program with Mexican scientists.