Development of Catalytic Coupling Methods via Unreactive C-C and C-N Bond Activation

Marquette University, Milwaukee WI

Investigators

Abstract

With the support of the Chemical Catalysis Program in the Division of Chemistry, Professor Chae Yi of Marquette University is studying new methods to upgrade petroleum and biomass-derived commodity chemicals into value-added materials using environmentally sustainable catalytic processes. The approach relies on the use of emerging concepts in transition-metal mediated catalysis that allow for molecular frameworks to be broken and reformed at bonds that have traditionally resisted manipulation. The studies will likely lead to fundamental advances in the field of catalytic bond activation and the knowledge gained is anticipated to lead to economic and environmental improvements in the preparation of complex organic molecules needed for the manufacture of pharmaceuticals and other valuable products. The broader impacts of the funded project shall extend to supporting summer internships that will allow for undergraduate students from local college STEM (science, technology, engineering and mathematics) programs to receive research experiences in the Yi laboratory. In addition, the award will enable Professor Yi to engage in outreach efforts at local high schools and colleges that will serve to promote careers in science and engineering for students with diverse backgrounds and many of whom belonging to groups underrepresented in the current STEM workforce. The funded project will focus on the development of new catalytic methods for organic synthesis based on the activation (rupture) of carbon-carbon and carbon-nitrogen bonds. The scope and mechanistic aspects of such processes as mediated by well-defined ruthenium catalysts with redox-active catechol ligands will be investigated and their synthetic applications for reforming biomass-derived organic commodities will be explored. During the course of these studies, the Yi laboratory will endeavor to develop a series of multi-component deaminative catalytic coupling methods that fuse carbonyl compounds with enamines as an efficient strategy for the elaboration of a variety of heterocyclic systems of relevance for the generation of pharmaceutically active substances. 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.