Development of efficient synthetic methods for Hydrogenation, Bromination and Nitrosation: Insights into catalyst design, reaction optimization, and mechanism investigation
- Yaghoubi, Mahshid
- Advisor(s): Baxter, Ryan RB
Abstract
This dissertation presents the development of new and cost-effective synthetic methods for various reactions under mild conditions using innovative reagents. The first chapter discusses the use of tetrahydroxydiboron as a novel hydrogen source for the hydrogenation of alkenes, followed by deuterium studies and selective reduction of nitriles to aldehydes. The second chapter details the development of a new bromination methodology using a cheap and easy-to-handle catalyst with excellent functional group tolerance at room temperature. The third chapter presents a novel synthetic method using a nitrosation reagent developed in our lab for the synthesis of novel triazenes and azo dyes, which are mostly reported for the first time. The final chapter focuses on the author's work as an intern at Vertex Pharmaceuticals, involving the synthesis of new libraries using High Throughput Experimentation, followed by screening assays, and hit identification. Supporting information is provided for the first chapter, including the characterization of products and nuclear magnetic resonance (NMR) spectra of the compounds produced through Pd-catalyzed hydrogenation of alkenes using tetrahydroxydiboron as a hydrogen atom source.