Author ORCID Identifier

Document Type


Date of Award

Fall 12-9-2022


Hydroetherification, Photoredox

Degree Name

Chemistry (BA, BS)



First Advisor

Dr. Jennifer Hirschi

Second Advisor

Dr. Brian Callahan

Third Advisor

Dr. Rebecca Kissling


Science and Mathematics

Subject Heading(s)

Etherification--Methods; Photochemistry--Research


The development of olefin hydroetherification reactions via the addition of an alcohol nucleophile and hydrogen atom across an unsaturated carbon-carbon bond has remained a sought- after synthetic transformation. The formation of ethers via this methodology has traditionally required the use of transition metals and/or harsh conditions to catalyze the reaction and is challenging to make selective. However, the Nicewicz laboratory has since developed an anti- Markovnikov intramolecular hydroetherification of alkenols using photoredox catalysis. With the mechanism of this pivotal transformation—and of photoredox reactions in general—being largely unexplored mechanistically, the Hirschi lab implemented experimental 13C kinetic isotope effects (KIEs) and density functional theory (DFT) to elucidate the mechanism of this transformation. A key finding was the role base additives play in the rate-limiting step of the reaction. Knowledge of the mechanism has enabled mechanism-driven reaction design to improve the rate, efficiency, yield, and capabilities of this reaction.

Available for download on Wednesday, December 31, 2025