Palladium-Catalyzed Decarboxylative alpha-Arylation

Author: Ian Anderson
Major: Chemistry
Approved: Spring 2017
Status: Completed

The original goal of this project was to further investigate the utility of palladium-catalyzed decarboxylative α-arylation reactions with new starting materials, mainly phosphonates, sulfones, and sulfoxides. Additionally, we intended to further perfect the existing reaction with esters and conduct kinetic trials of the esters’ decarboxylation. Work was done using standard undergraduate-level synthetic organic lab techniques. Data was primarily analyzed by using NMR spectroscopy and Gas Chromatography. Phosphonates and Sulfoxides did not react in significant yields. Sulfones underwent decarboxylation but did not couple to palladium in significant yields. Data was collected on ester decarboxylation kinetics in relation to the addition of zinc catalyst and the data was inconsistent. Future work will likely be in an entirely different direction than decarboxylative reactions.

Full Project Report