Visible Light Promoted Alkylation of Imines using a Photocatalyst
Session Title
Poster Session 2
Faculty Mentor
James Hanna, Ph.D.
College
College of Arts and Sciences
Department
Chemistry, Physics, Geology, & the Environment
Abstract
Use of light as an energy source for the synthesis of organic compounds has been occurring for millions of years in the form of photosynthesis. However, within the last decade visible-light photoredox catalysis has been developed into a practical and efficient method to synthesize a large variety of organic molecules. Many of these reactions employ a transition metal complex photocatalyst based on ruthenium or iridium. This transition metal complex can absorb visible light to promote the generation of radicals through a series of single-electron-transfers with organic substrates, allowing organic synthesis to occur. However, transition metal photocatalysts tend to be expensive, prompting our group to investigate the use of less expensive, commercially available organic photocatalysts in our studies of the visible light promoted alkylation of imines with potassium organotrifluoroborates. In this presentation, the synthesis of amines using radicals generated from the organic photocatalyst, 9-mesityl-10-methylacridinium tetrafluoroborate (Mes-Acr-Me) and potassium organotrifluoroborates, along with their subsequent addition to imines, will be explored.
Previously Presented/Performed?
NC Photochem, Columbia, SC, October 2022 | Winthrop University Showcase of Winthrop University Undergraduate Research and Creative Endeavors, Rock Hill, SC, April 2023
Type of Presentation
Poster presentation
Grant Support?
Supported by the American Chemical Society Petroleum Research Fund (58270-UR1) and an SC-INBRE grant from the National Institute for General Medical Sciences (P20GM103499).
Start Date
15-4-2023 12:00 PM
Visible Light Promoted Alkylation of Imines using a Photocatalyst
Use of light as an energy source for the synthesis of organic compounds has been occurring for millions of years in the form of photosynthesis. However, within the last decade visible-light photoredox catalysis has been developed into a practical and efficient method to synthesize a large variety of organic molecules. Many of these reactions employ a transition metal complex photocatalyst based on ruthenium or iridium. This transition metal complex can absorb visible light to promote the generation of radicals through a series of single-electron-transfers with organic substrates, allowing organic synthesis to occur. However, transition metal photocatalysts tend to be expensive, prompting our group to investigate the use of less expensive, commercially available organic photocatalysts in our studies of the visible light promoted alkylation of imines with potassium organotrifluoroborates. In this presentation, the synthesis of amines using radicals generated from the organic photocatalyst, 9-mesityl-10-methylacridinium tetrafluoroborate (Mes-Acr-Me) and potassium organotrifluoroborates, along with their subsequent addition to imines, will be explored.
