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

Instructions

Student presentations must have a faculty sponsor.

Abstracts must include a title and a description of the research, scholarship, or creative work. The description should be 150-225 words in length and constructed in a format or style appropriate for the presenter’s discipline.

The following points should be addressed within the selected format or style for the abstract:

A clear statement of the problem or question you pursued, or the scholarly goal or creative theme achieved in your work.
A brief comment about the significance or uniqueness of the work.
A clear description of the methods used to achieve the purpose or goals for the work.
A statement of the conclusions, results, outcomes, or recommendations, or if the work is still in progress, the results you expect to report at the event.

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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:

Jun Wang
Kim Instenes
John Kirk
Nora Nickels
Andrew Pustina
James Ripley

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.