Excellence in Research: Unlocking the Synthetic Power of Regioselective and Stereoselective Carbon Carbon Bond Formations for Multicomponent Reactions in Heterocycle Synthesis

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The HBCU Excellence in Research program supports the project by Professor Fenghai Guo. Professor Fenghai Guo is a faculty member in the Department of Chemistry at Winston Salem State University. In the proposed project, Professor Guo and his group are developing new reactions that allow for efficient construction of new carbon-carbon bonds. The bonds are found in the nitrogen, sulfur, and oxygen based ring skeletons that form the core of many medicinally active molecules. The chemistry takes advantage of metal-based reagents that lower the energetic barrier for reactions that assemble larger molecules from multiple smaller, more readily available building blocks in a single step. In addition to these scientific goals, the research project provides research experiences for STEM undergraduates who are from underrepresented groups. To that end, Professor Guo's group is ideally located at Winston Salem State University. In addition to working with the undergraduate students at Winston Salem State University, the PI and his group are involved in outreach activities that provide high school interns with opportunities to pursue research in the area of synthetic chemistry. Carbon carbon bond formation is very valuable in forming the carbon skeletons of complex heterocycles. In this project, Professor Guo is developing multicomponent reactions that consist of tandem 1,4- and 1,6-conjugate addition-acylation sequences and tandem 1,4-, 1,6-conjugate additions coupled with oxidative coupling reactions. The reactions lead to the generation of multiple C-C bonds and stereocenters. The research is generating new knowledge in terms of the selectivity available to metal catalyzed conjugate addition reactions and the generation of new heterocyclics. The utility of the method is being illustrated by its application to the synthesis of bioactive, complex heterocyclic ring systems. The educational Broader Impact of the work centers on the opportunities it is providing for students from underrepresented groups to gain research experience in synthetic chemistry. Winston Salem State University serves as a gateway to the sciences for many African American and underrepresented minority students. In this way, the Guo group is ideally positioned to have a significant educational Broader Impact.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.