Visible Light Promoted Alkylation of Imines using a Photocatalyst

Submitting Student(s)

Marcus Schlueter
Ryan Wernsman

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

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Apr 15th, 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.