Celebration of Scholars
Radical Bromination Using Photoredox Catalysis
Name:
Sydney Redlin
Major: Biology
Hometown: Kenosha
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Name:
Jacquie Chippeaux
Major: Biology
Hometown: Appleton
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Major: Chemistry
Hometown: St. Charles
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Abstract
Radical bromination is an important reaction in organic synthesis because it converts a normally unreactive C–H bond of an alkane to a C–Br bond of an alkyl halide. Alkyl halides are versatile synthetic intermediates that can be used to form many other common functional groups. Many current methods for radical bromination are costly, inefficient, and require toxic reagents and high energy UV light. The goal of our research is to develop new methods for radical bromination using photocatalysis. Photocatalysis is a more sustainable approach to radical bromination, since it minimizes the use of toxic reagents and allows for reactions to be performed using sunlight as the energy source. Current efforts in our lab are focused on benzylic bromination using substrates like ethyl benzene and a derivative of ibuprofen, methyl 2-(4-isobutylphenyl) propanoate. Using a photocatalyst called tetra-n-butylammonium decatungstate, light from a reptile lamp, and a variety of radical bromine sources in acetonitrile, we have achieved benzylic bromination in low to moderate yields. Current efforts are focused on optimizing the reaction conditions to increase the yield. We have also observed the formation of an amide side product that we are exploring further in the hopes of developing a benzylic amidation reaction.
Submit date: Feb. 26, 2021, 1:17 p.m.