EAPSI: Catalyst Development for the Synthesis of Acylated Aromatic Compounds

Konev Mikhail O, Irvine CA

Investigators

Abstract

Carbon-carbon bond forming reactions are ubiquitous in the realm of synthetic chemistry, allowing the strategic construction of pharmaceuticals and materials alike. Although many methods exist, simple, efficient, and mild conditions are desirable for ease of preparation and economic sustainability. Metal-catalysts are constantly being developed to satisfy these needs, and the design of new catalysts can provide further progress towards this endeavor. The host researcher, Dr. Tobisu Mamoru at Osaka University, has recently reported a carbon-boron bond forming reaction to yield valuable chemical building blocks. Under Dr. Tobisu?s guidance, the research will optimize the first generation of catalysts for application to carbon-carbon bond formation. This work will lead to the development of synthetic methods useful for the efficient preparation of pharmaceutically relevant acylated aromatics. This project aims to develop a rhodium catalyst for the mild C-O acylation of pyridyloxy directing groups. Pyridyl directing groups have seen great success in the regioselective C-H activation of aromatic substrates, however, their removal is limiting to their utility in synthetic applications. Dr. Tobisu has recently developed the corresponding C-O borylation reaction, setting the precedent for the proposed transformation. The EAPSI project will allow for the synthesis of acylated aromatics, which are useful intermediates for chemical synthesis and are prevalent among natural products and pharmaceuticals. Development of such catalysts will also further the fundamental understanding of reactivity of rhodium complexes. This award under the East Asia and Pacific Summer Institutes program supports summer research by a U.S. graduate student and is funded jointly by NSF and the Japan Society for the Promotion of Science.