Title of Abstract

Photoredox Mediated Alkylation of Imines with Potassium Organotrifluoroborates in the Presence of an Organic Photocatalyst

Poster Number

56

Submitting Student(s)

Molly Quetel

Faculty Sponsor (for work done with a non-Winthrop mentor)

James Hanna, Jr., Ph.D. & Cheryl Fortner-Wood, Ph.D.

College

College of Arts and Sciences

Department

Chemistry, Physics & Geology

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

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Apr 15th, 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.