Photoredox Mediated Alkylation of Imines with Potassium Organotrifluoroborates in the Presence of an Organic Photocatalyst
Poster Number
56
Session Title
Poster Session 2
College
College of Arts and Sciences
Department
Chemistry, Physics, Geology, & the Environment
Abstract
During the last 10-12 years, visible-light photoredox catalysis (VLPC) has been developed into a practical method to achieve a wide variety of synthetic transformations. The approach often involves a transition metal complex of ruthenium or iridium, which, upon absorption of visible light, can participate in a series of single-electron-transfer (SET) events with organic substrates, leading to productive chemistry. However, these transition metal catalysts can be quite expensive, which led our group to investigate the use of less expensive organic photocatalysts in our studies of the alkylation of aryl imines with potassium organotrifluoroborates. In this presentation, the application of a widely used organic photocatalyst, 9-mesityl-10-methylacridinium tetrafluoroborate ( Mes-Acr-Me), will be explored; data from optimization experiments, along with those from the scope and limitations studies including both imines and organotrifluoroborates, will be surveyed. In addition, results from Stern-Volmer quenching studies – carried out to verify the initial electron transfer event of the proposed mechanism – will be discussed.
Start Date
15-4-2022 12:00 PM
Photoredox Mediated Alkylation of Imines with Potassium Organotrifluoroborates in the Presence of an Organic Photocatalyst
During the last 10-12 years, visible-light photoredox catalysis (VLPC) has been developed into a practical method to achieve a wide variety of synthetic transformations. The approach often involves a transition metal complex of ruthenium or iridium, which, upon absorption of visible light, can participate in a series of single-electron-transfer (SET) events with organic substrates, leading to productive chemistry. However, these transition metal catalysts can be quite expensive, which led our group to investigate the use of less expensive organic photocatalysts in our studies of the alkylation of aryl imines with potassium organotrifluoroborates. In this presentation, the application of a widely used organic photocatalyst, 9-mesityl-10-methylacridinium tetrafluoroborate ( Mes-Acr-Me), will be explored; data from optimization experiments, along with those from the scope and limitations studies including both imines and organotrifluoroborates, will be surveyed. In addition, results from Stern-Volmer quenching studies – carried out to verify the initial electron transfer event of the proposed mechanism – will be discussed.
