With this CAREER Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Sergey V. Pronin of the Department of Chemistry at the University of California Irvine. Professor Pronin and his students are developing new methods for the direct conversion of compounds that contain a double bond between two carbon atoms (i.e., alkenes) to compounds that contain nitrogen (amines), a oxygen-hydrogen groups (alcohols), and their derivatives. The reaction conditions are mild and use environmentally-abundant materials, making the new synthetic routes attractive for conserving both energy and critical elements. These new molecules are valuable chemicals used extensively in industry, especially the pharmaceutical industry. The chemical transformations being studied are a long-standing challenge in the field of organic chemistry. This research is taking advantage of underexplored patterns of chemical reactivity and producing new and general solutions to these problems. Professor Pronin's laboratory host ?Day at College? events as a part of the Laboratory Experiments and Activities in the Physical Sciences (LEAPS) program at UCI, which is aimed at educating middle school students about the opportunities that exist for them in the physical sciences. In collaboration with other faculty at UCI, the research team recruit and host students from a local community college with a large population of underrepresented minority students, Santiago Canyon College, for ten weeks during the summer to provide research experiences in the field of synthetic organic chemistry. This program is expected to increase awareness of minority students for STEM research and job opportunities. The research is also providing a rich training ground for the next generation of chemists, generating opportunities for students from community colleges with limited engagement in chemistry research.
This research is leveraging radical-polar crossover reactivity and developing new enantioselective methods for the hydrofunctionalization of alkenes via earth-abundant cobalt species. These transformations combine facile hydrogen atom transfer events with oxidation of the resulting alkyl radicals and related intermediates to the corresponding carbocations or their synthetic equivalents. These species can then undergo reactions with nucleophiles to generate new functional groups. The combined process serves as an equivalent of Bronsted acid-catalyzed hydrofunctionalizations but proceeds in the absence of an acid. The exceptionally mild conditions of these reactions accommodate a broad substrate scope and facilitate development of the corresponding enantioselective reactions. Overall, this research is providing direct and general access to valuable scalemic building blocks from readily available starting materials and producing new knowledge of the fundamental reactivity of carbocations and related electrophilic intermediates. The research is also providing a rich training ground for the next generation of chemists, generating opportunities for students from community colleges with limited engagement in chemistry research, and increasing awareness of middle school students to future career options in STEM fields.
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.