Cross-nucleophile Coupling and Homologation Reactions of Organoboron Compounds

With support from the Chemical Synthesis Program in the Division of Chemistry, Professor Gojko Lalic at the University of Washington is studying the development of new reactions for the synthesis of organic molecules using organoboron compounds and transition metal catalysis. The project is advancing more efficient transformations of common starting materials into more valuable targets, complementing existing methods. These reactions are providing a new approach to forming carbon-carbon bonds, critical for constructing large organic molecules. Beyond practical applications in organic synthesis, the fundamental properties and reactivity of organoboron compounds are being investigated and expanded in these studies. An essential part of the project is its outreach initiative, which fosters connections with the local community. Dr. Lalic's team engages elementary and high school students through activities that inspire interest in science, technology, engineering, and mathematics (STEM) careers. Organoboron compounds are valuable synthetic building blocks due to their availability, stability, and versatile reactivity. Continued advances in the synthetic applications of these compounds is critically important to support the pharmaceutical industry, medicinal chemistry, the synthesis of agrochemicals, and material science. Prof. Lalic and his research team are creating more effective tools for synthesizing complex organic molecules by exploring two new classes of chemical reactions. The first is a new type of cross-coupling reaction using two nucleophilic coupling partners that leverages the ambiphilic nature of organoboron compounds and the ability of transition metal complexes to modulate their reactivity. The second focuses on innovative strategies for homologating organoboron compounds via formal insertion of C2 fragments into carbon-boron bonds. Notably, this C2 fragment insertion involves an unusuallly facile activation of carbon-carbon bonds. Integral to this work are outreach activities, which are designed in collaboration with the local community, to promote science education and engagement. 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.