New Catalytic Transformations for the Synthesis of Alkenes and Organoboron Compounds

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With the support of the Chemical Catalysis Program in the Division of Chemistry, Gojko Lalic of the University of Washington is studying new reactions for the synthesis of organic molecules. The goal of this research is to provide more efficient access to complex molecules used in preparation of fine chemicals and pharmaceuticals. The proposed new reactions use common starting materials and transform them into more valuable compounds, utilizing catalysis by earth-abundant metals, copper and nickel, and with attention to developing efficient catalytic processes. Dr. Lalic and his group have built a number of outreach activities around their research. They have established a strong working relationship with their local community, by reaching out to elementary and high school students to promote awareness of and exposure to science and technology. A wide range of activities, including regular participation in science classes at local high schools, are designed to reach students underrepresented in science and promote careers in science, technology, engineering, and mathematics (STEM) disciplines.The proposed research will explore two new classes of organic reactions. The first class will provide a general strategy for regio- and diastereoselective synthesis of trisubstituted alkenes. The approach is based on the use of a simple directing group to control regioselectivity in the hydroalkylation of disubstituted alkynes. The second class of reactions will explore new strategies for the synthesis and the activation of borate complexes. Most previous studies of borate complexes have relied on stoichiometric reactions of organometallic reagents to access the borate complexes. Proposed are new catalytic methods for borate synthesis from simple organoboranes and a variety of unsaturated compounds. The proposed research will also explore transformations in which a metal catalyst both promotes the formation of the borate complex and activates it for a subsequent reaction. In addition to the development of new synthetic methods, the Lalic team seeks to provide new insight into the fundamental reactivity of organometallic complexes.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.