2024 Theses Doctoral

Rh(III)-Catalyzed Alkene Amidation Reactions: Development and Mechanistic Studies

Wagner-Carlberg, Noah

Due to their large-scale production by the oil refinement industry, alkenes are some of the most ubiquitous starting materials in organic chemistry. The synthesis of many building block chemicals can be traced back to an alkene functionalization reaction. One alkene functionalization that remains underexplored is the introduction of amides. Amide formation is incredibly important, as it is the most common functional group found in bioactive molecules, and amide bond formation is the most common reaction in medicinal chemistry.

My thesis will discuss several new methodologies for converting simple alkene starting materials into value-added amide products. First, I will talk about an anti-Markovnikov alkene hydroamidation procedure. Next, I will talk about leveraging chain walking to enable remote hydroamidation of internal alkenes. Finally, I will talk about alkene difunctionalization via nucleometalation to yield heterocyclic products with amides appended. In addition to reaction development, much of the talk will focus on elucidating and studying the mechanisms of each of these transformations.