Showcase of Undergraduate Research and Creative Endeavors (SOURCE)

Visible-Light Mediated Radical Additions of Aldehydes with Organotrifluoroborates

Recently, our laboratory has been exploring the visible-light promoted radical additions to aldehydes with potassium organotrifluoroborate compounds. If our approach is successful, it will serve as a novel approach to aldehyde radical addition and hinder the reversibility of unstable alkoxy radicals. Furthermore, an emphasis has been placed on the use of a photo-regenerated organic catalyst (9-Mesityl-10-methylacridinium tetrafluoroborate). The tandem use of an organic photocatalyst and photocatalytic cycle will allow for a shift away from the use of toxic reagents and molar amounts of substances, respectively. As a result, various functionally substituted aldehydes can be synthesized marginally more sustainably. Further, a series of optimization studies will be conducted to find favorable conditions at which the subsequent reactions will be conducted under. Once the optimal conditions are set, aldehydes and organotrifluoroborates with varying functional substitutions (i.e. aryl-, alkyl-, allyl-, and groups with varying electronic effects) will be tested to obtain yield via an internal standard method of NMR spectroscopy. Each concurrent experiment will uncover interaction between various sterics and electronics within this photocatalytic process. Thus, these interactions and yields will be documented and reaction scheme will be proposed.