Camille Rubel

Regioselective Silylation of Fluorinated Arenes

The substitution of fluorine atoms for hydrogen atoms in drug candidates has been shown to improve the biostability of those molecules. However, few reported methods exist that fluorinate complex organic molecules with high selectivity. An alternate approach to the synthesis of fluorinated drug candidates is the addition of functional groups to compounds that contain fluorine. Thus, the functionalization of fluorinated compounds would enable the discovery of improved drug candidates. Recent research has described the catalytic silylation of aryl C-H bonds. Aryl silanes are bench-stable, and the silyl group can be transformed into many other functional groups. However, current methods for the silylation of C-H bonds of fluorinated arenes produce mixtures of products, with silylation occurring both ortho and meta to fluorine. Our research seeks to develop new catalysts for the regioselective and functional group tolerant silylation of aryl C-H bonds located ortho or meta to fluorine. We aim to design new catalysts for this transformation and to employ the catalysts to synthesize pharmaceutical analogs containing novel fluorine substitution patterns.

Message to Sponsor

Thank you to Rose Hills for funding my summer research. The fellowship provided me the opportunity to perform chemistry research for the first time. I was able to fully devote myself to research as a result of the generous funding provided, so my laboratory skills greatly increased. I look forward to using the skills I gained to continue for the next two years with research in the field of organometallic chemistry. The experience this summer allowed me to implement the knowledge I have been learning in the classroom, and the ability to apply my skills granted me a sense of purpose in my academic pursuits.
  • Major: Chemistry
  • Sponsor: Rose Hills Experience
  • Mentor: John Hartwig