RUI: Metal-Catalyzed Borylation: Chiral Ligand Synthesis to New Tools in Organogermanium Chemistry

Dr. Timothy Clark of the University of San Diego will develop new reactions and tools designed to simplify access to complex and biologically important compounds, including pharmaceuticals. The synthetic strategy will focus on installing and using carbon-boron bonds to access valuable intermediates. These tools will be developed with an eye toward advanced manufacturing of pharmaceuticals and materials and in applications to medicinal chemistry. In addition to the broader impacts related to medicinal, material, and pharmaceutical synthesis, the project will provide training for nine undergraduate students in chemical synthesis. The project will also fund a postdoctoral research associate who aspires to be a professor of chemistry, providing mentored training in chemical research and in teaching. Finally, the award will fund an exchange with collaborator Dr. Donald Watson of the University of Delaware where three undergraduate students from the University of San Diego will spend half of a summer working with Dr. Watson and three graduate students from the University of Delaware will spend half of a summer working with Dr. Clark. This exchange provides opportunities for the students involved to explore educational and career opportunities in very different research environments for career discernment. The project will utilize oxidative homocoupling to simplify access to chiral biaryl bisphosphines, ubiquitous ligands in asymmetric catalysis. Specifically, bisphosphines possessing ortho substituents are targeted for enhanced asymmetric catalysis. Oxidative homocoupling will also be applied to a series of aryl boronate esters with the goal of determine the role and scope of adjacent substituents that can support the oxidative homocoupling. Finally, a systematic approach to the C-H borylation of aryl germanes will be examined with the goal of providing efficient access to arenes possessing both a boron and germanium substituent, which can be reacted orthogonally for target-directed synthesis. 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.