Event Title

Visible Light Promoted Reactions of Potassium Organotrifluoroboratesto Carbonyl Compounds

Faculty Mentor

Dr. James M. Hanna, Jr.

College

College of Arts and Sciences

Department

Chemistry, Physics and Geology

Location

DiGiorgio Campus Center, Room 222

Start Date

22-4-2016 1:25 PM

End Date

22-4-2016 1:40 PM

Description

Visible light photoredox catalysis has become a significant area of organic chemistry research since 2008 when the Macmillan, Yoon, and Stephenson groups independently employed the redox properties of photoexcited Ru(bpy)32+ in the development of novel approaches to several important synthetic transformations. This new paradigm has since been exploited in the creation of new synthetic pathways, allowing access to transformations not previously available. Our research group is interested in the application of this strategy to reactions of potassium organotrifluoroborates, which have been shown to be oxidized to organic radicals by excited-state iridium complexes. In our laboratory, using the addition of potassium benzyltrifluoroborate to benzaldehyde as a model system, we have found that the desired coupling is promoted by the use of visible light in the presence of a suitably ligated iridium catalyst, whereas in the absence of the catalyst, very little to no coupling occurs. This approach has potential advantages over typical reactions of organometallics with carbonyl compounds due to the mild conditions employed and the functional group tolerance of potassium organotrifluoroborates. In this presentation, we will describe our progress in this area.

Previously Presented/Performed?

South Carolina Academy of Science Annual Meeting, Winthrop University, April 2016

Grant Support?

Supported by a grant from the National Institutes of Health IDeA Networks for Biomedical Research Excellence (NIH INBRE)

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Apr 22nd, 1:25 PM Apr 22nd, 1:40 PM

Visible Light Promoted Reactions of Potassium Organotrifluoroboratesto Carbonyl Compounds

DiGiorgio Campus Center, Room 222

Visible light photoredox catalysis has become a significant area of organic chemistry research since 2008 when the Macmillan, Yoon, and Stephenson groups independently employed the redox properties of photoexcited Ru(bpy)32+ in the development of novel approaches to several important synthetic transformations. This new paradigm has since been exploited in the creation of new synthetic pathways, allowing access to transformations not previously available. Our research group is interested in the application of this strategy to reactions of potassium organotrifluoroborates, which have been shown to be oxidized to organic radicals by excited-state iridium complexes. In our laboratory, using the addition of potassium benzyltrifluoroborate to benzaldehyde as a model system, we have found that the desired coupling is promoted by the use of visible light in the presence of a suitably ligated iridium catalyst, whereas in the absence of the catalyst, very little to no coupling occurs. This approach has potential advantages over typical reactions of organometallics with carbonyl compounds due to the mild conditions employed and the functional group tolerance of potassium organotrifluoroborates. In this presentation, we will describe our progress in this area.