Research Seminar Abstract

Compounds containing bonds with combinations of boron, silicon, and tin are attractive main group element transfer reagents. These bonds are activated via a nucleophilic attack that facilitates the release of one of the bonded main group moieties with enhanced nucleophilicity towards unactivated electrophiles. We wondered if this interesting reactivity platform could be generalized to exploit new bond transformations, such as amination. Amines are ubiquitous in natural products and pharmaceuticals such as Flunarizine, Naftifin, and Triprolidine. Since amines can act as both a hydrogen bond acceptor and donor, they are often key contributors in drug-receptor interactions. Additionally, incorporating amines in drugs can aid in increasing the basicity and solubility of the molecule. Due to the importance of amines, the development of simple methods to directly install amines are in high demand. Current methods to incorporate amines into molecular scaffolds involve transition metal catalysis and often require activated or prefunctionalized starting materials. A method that installs amines from unactivated substrates, such as allylic alcohols, would be a significant advancement to the field. This can be envisioned by exploiting the innate reactivity of an allylic alcohol, combined with an aminating reagent that facilitates amine bond formation when activated.