Camille Rubel Rose Hills
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.