#63: Radical Halogenation Using Photocatalysis — Presentation Detail — Celebration of Scholars

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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.

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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

#63: Radical Halogenation Using Photocatalysis

Name: Anna Benz-Weeden
Major: Chemistry and Biology
Hometown: Orland Park, IL
Faculty Sponsor:
Other Sponsors:
Type of research: SURE
Funding: SURE

Abstract

Radical halogenation is a fundamental transformation in organic synthesis that converts a C–H bond to a C–X bond. Traditionally, radical halogenation has been accomplished using harsh reaction conditions like ultraviolet light and toxic reagents. In this research, we are exploring a new, more sustainable approach to radical halogenation using photocatalysis. Specifically, we are investigating the radical halogenation of organic molecules using the photocatalyst tetra-n-butylammonium decatungstate (TBADT) and a variety of halogen sources. In the presence of light, TBADT becomes excited and abstracts a hydrogen atom from the starting material to form an alkyl radical. The radical intermediate may then abstract a halogen atom from the halogen source to form a C–X bond. Optimization of the reaction conditions revealed diethyl bromomalonate as a promising bromine source for radical bromination in combination with the TBADT catalyst. Preliminary substrate scope investigations show that a variety of C–H bonds, both activated and inactivated, can be brominated using this method. The selectivity of the radical bromination was also explored.

Poster file