Visible Light Promoted Reactions of Potassium Organotrifluoroboratesto Carbonyl Compounds
College
College of Arts and Sciences
Department
Chemistry, Physics, Geology, & the Environment
Faculty Mentor
Dr. James M. Hanna, Jr.
Abstract
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)
Start Date
22-4-2016 1:25 PM
End Date
22-4-2016 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.
