Celebration of Scholars
Radical Chlorination using Visible Light Photocatalysis
Name:
David Wilson
Major: Chemistry
Hometown: Batavia, IL
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Name:
Anna Benz-Weeden
Major: Chemistry & Biology
Hometown: Orland Park, IL
Faculty Sponsor:
Other Sponsors:
Type of research: Independent research
Abstract
Radical chlorination is an important transformation in organic synthesis. Traditionally, radical chlorination has been accomplished using harsh reaction conditions like ultraviolet light and toxic reagents like chlorine gas. Our lab is exploring a new, more sustainable approach to radical chlorination using photocatalysis. In photocatalysis, the reaction is exposed to visible light, which excites the catalyst and allows the reaction to proceed. The current conditions being examined in the reaction are the use of a tungsten photocatalyst, TBADT, ethyl benzene as the substrate being chlorinated, and a range of chlorine sources in solution with acetonitrile. In the presence of visible light, the tungsten catalyst becomes excited and reacts with the ethyl benzene, forming a radical intermediate on the benzylic carbon. The radical intermediate then reacts with the chlorine source and forms a carbon chlorine bond. The optimization of reaction conditions is the main point of investigation. One variable that is being examined is the effectiveness of the chlorine radical source. So far, we have observed that different chlorine radical sources produce a mono-chlorinated product. The focal point of this investigation is to further optimize the conditions of the reaction to improve the yield and apply it to a variety of reagents, including natural products.
Submit date: Feb. 25, 2021, 8:51 p.m.