Class of 2010
- Major: Chemistry
- Minor: Biology
- Resident Assistant
- James R. Miller ’51 Award for Excellence in Chemistry
Senior Capstone Experience
Progress towards a new palladium catalyzed indenoannulation method for polycyclic aromatic hydrocarbons
Advisor: Dr. Aaron Amick
Indenoannulation reactions have proven to be a valuable way to build complexity into flat and bowl shaped polycyclic aromatic hydrocarbons (PAHs), which is vital toward the chemical synthesis of a carbon nanotube end-cap. All of the current methods have imperfections and a new approach that will produce the same product but eliminate the need for long reaction times and the use of expensive reagents is needed.
The goal of this research is to use the Buchwald-Hartwig coupling to install cyclohexanone units onto PAHs in a one step procedure, convert them to enol-triflates or vinyl halides, and then perform indenoannulation by using a palladium catalyst to promote cyclization. The final step of this synthesis is to use 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to rearomatize the indenoannulated product produced in the previous step. This method provides soluble intermediate that can be purified and characterized before rearomatization. Current work has focused on expanding this method to other substrates.
- Doctor of Pharmacy Program at Duquesne University Mylan School of Pharmacy