Event

Building molecular complexity through visible light photocatalysis:

Spotlight on undergraduate research

Emily C. McLaughlin

Associate Professor of Chemistry

Chemistry and Biochemistry Program, Bard College, Annandale-on-Hudson, NY 12504

-Organic photochemical transformations have been utilized extensively in the synthesis of biologically active natural products and organic frameworks. In this work, we explore the utility of visible light photocatalysis in both carbon-nitrogen (C-N) and carbon-carbon (C-C) bond-forming reactions, targeting aziridine and cyclobutane ring systems, respectively. Although these motifs can be prepared through cycloadditions promoted by ultraviolet (UV) light, UV light sources are expensive, hazardous to use, and often lead to unwanted reactivity though high-energy intermediates. Our methods focus on the development of photocycloaddition protocols that employ lower-energy visible light (blue LEDs). Harnessing this energy with iridium bypyridyl transition metal complexes, we synthesize aziridines from electrophilic amine and alkene starting materials and highly functionalized cyclobutanes from vinylogous esters and enones. Central to the undergraduate research experience in our lab, is student-driven experimental design and analysis of results to better understand the mechanistic nuances of photocatalytic reactions.

https://www.bard.edu/academics/faculty/details/?id=2363

Host Prof. Jeff Winkler