Date of Award
Chemistry and Biochemistry
Joseph Badillo, PhD
Cecilia Marzabadi, PhD
Cosimo Antonacci Ph.D.
Photoacid generator, proton-transfer, conjugate addition, carbocation catalysis
Proton transfer is essential in many natural and chemical processes, and photoacids that undergo proton dissociation or generation upon photoirradiation can be beneficial for use in acid-sensitive reactions. This work describes the use of photoacid generators (PAGs) as tools for organic synthesis, generating strong acids upon light absorption catalyzing Michael addition reactions. Specifically, visible-light-induced PAGs were used to facilitate the 1,4-conjugate addition between indoles and vinyl ketones. Furthermore, carbocations have gained attention as Lewis acid catalysts in a variety of reactions providing good selectivity and yields. We also demonstrate the viability of in-situ photoredox-generated carbocation catalysis in the context of conjugate addition reactions.
Salem, Zena M., "Visible Light Photoacid Generator Catalyzed Michael Additions & In-situ Photoredox Generated Carbocation Catalysis" (2023). Seton Hall University Dissertations and Theses (ETDs). 3125.