Design, Synthesis, and Kinetic Study of the First Generation Phenyloxadiazole Compounds and the Second Generation Phenyloxadiazole Compounds and Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex
Date of Degree
Wayne W. Harding
Design, Synthesis, Kinetic Study, Phenyloxadiazole, Hydroboration, Manganese Complex
This thesis focuses on two projects. In the first project, my goal was to discover a new variant of phenyloxadiazole compounds that could exhibit increased thiol-reactivity during bioconjugation processes. To achieve this, I synthesized several phenyloxadiazole derivatives and subjected them to NMR kinetic studies to assess their reactivity with a model thiol. Based on the results, I was able to identify a phenyloxadiazole analog that demonstrated enhanced reactivity, which included a chlorine atom located in the meta-position of the phenyl ring.
I provided a detailed description of the synthesis and characterization of the newly discovered phenyloxadiazole analog and demonstrate its reactivity with thiol. The findings of this study have significant implications for the development of new and improved bioconjugation reagents. The results indicate that the identified phenyloxadiazole analog has the potential to become a valuable tool for bioconjugation processes, offering enhanced reactivity and improved performance over existing reagents.
In the second project, to achieve selective hydroboration of alkenes, ketones, and aldehydes, manganese complexes have been synthesized using low-cost and readily available ligands such as 2,2':6',2"-terpyridine and its derivatives. These complexes are highly efficient and offer excellent performance. A new earth-abundant manganese catalyst has been developed, which has demonstrated high Markovnikov regioselective hydroboration of styrene compounds, as well as outstanding chemoselective hydroboration of ketones over alkenes. The use of such a catalyst could pave the way for the development of new and improved hydroboration techniques in the future, with significant implications for asymmetric reduction of styrene compounds and ketones.
Zeng, Haisu, "Design, Synthesis, and Kinetic Study of the First Generation Phenyloxadiazole Compounds and the Second Generation Phenyloxadiazole Compounds and Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex" (2023). CUNY Academic Works.