Exploring oxygen nucleophiles in palladium-catalyzed difunctionalization reactions

Author: Alec Carlson
Major: Biochemistry
Approved: Spring 2019
Status: Completed

Palladium chemistry, specifically the use of it as a catalyst in an organic setting, has interested the scientific community for most of the latter half of the 20th century.The focus is mostly centered around the transition metal’s ability to form carbon-carbon bonds, a process that is extremely hard to carry out predictably under mild conditions.Previous research within our lab showed the production of a novel palladium-catalyzed aromatic translocation, which concluded by means of aβ-hydride elimination.However,with the presence of water, the reaction forwent β-hydride elimination in favor of a nucleophilic addition by water on the ɑ-carbon. The nucleophilic addition of alcohols was tested in accordance with the previous results and success was found in all primary and secondary alcohols, with tertiary alcohols too hindered by sterics to allow for the addition.Successful additions were also been in complex bifunctional alcohols, e.g. 2-methoxyethanol, showing great synthetic promise for future trials aimed at pushing the limits of this reaction.