Triarylphosphonium Salts as Radical Precursors using Photoredox Catalysis — Presentation Detail — Celebration of Scholars

Additional Information

More information is available at carthage.edu/celebration-scholars/. The following are members of the Research, Scholarship, and Creativity Committee who are eager to listen to ideas and answer questions:

Thomas Carr
Katherin Hilson
Kim Instenes
John Kirk
Sarah Terrill

Triarylphosphonium Salts as Radical Precursors using Photoredox Catalysis

Name: Jonathan Ramirez
Major: Chemistry
Hometown: Zion,IL
Faculty Sponsor:
Other Sponsors:
Type of research: SURE
Funding: SURE

Name: Andrew Boldt
Major: Chemistry
Hometown: Davenport, Ia
Faculty Sponsor:
Other Sponsors:
Type of research: SURE
Funding: SURE

Abstract

Photoredox catalysis is a powerful tool used to form carbon radicals. These highly reactive carbon radicals can be generated from triphenylphosphonium salts through cleavage of the carbon-phosphorus bond. By using visible light as an energy source instead of heat or UV light, these reactions proceed in a more sustainable manner. A series of experiments were conducted testing the reactivity of the phosphonium salts under photoredox conditions. Initial experiments indicated that dimerization of the benzyl substrate was the major reaction pathway. Different aspects of the reaction were optimized such as light, catalyst, atmosphere, etc. Once optimal conditions were set, the substrate scope was explored. Preliminary experiments have demonstrated that substrates with electron-donating groups prefer to dimerize and substrates with electron-withdrawing groups undergo reduction. A natural product, brittonin A, was also synthesized using this method.

Submit date: April 1, 2020, 10:13 p.m.