Associate Professor of Chemistry
B.S., Rhodes College, 1998
Ph.D., University of Illinois at Urbana-Champaign, 2002
For more details, see my curriculum vitae.
Research and Activities
My current research is focused on developing transition metal reagents for perfluoroalkylation of aromatic compounds. Fluorinated organic molecules comprise over 20% of pharmaceuticals and 40% of agrochemicals. The application of fluoroorganics to various biological problems has been encouraged by their favorable properties, including increased stability and lipophilicity in vivo. (See Chem. Eng. News, 84, 23, 15 and 27 for recent highlights of fluorine chemistry in biologically-active compounds.)
Although several methods to install perfluoroalkyl groups on arene rings have been described, a mild, efficient system tolerant of a broad range of substrates has not yet been described. C-H bond activation could provide a route for directly synthesizing perfluoralkyl analogues of compounds with established bioactivity. Some systems capable of perfluoroalkylating arenes via C-H activation are known, although all require reagents that are difficult to synthesize, suffer from limited substrate scope, or give poor yields. It is also known that compounds of the formula Fe(CnF2n+1)(I)(CO)4 transfer perfluoroalkyl ligands to arenes and heteroarenes upon reaction with AgF, although the yields and selectivities for the perfluoroalkyl transfer reactions are not acceptable for synthetic applications. These reactions can be performed at or near room temperature and in the absence of strong acid or base, which could allow this reaction to be used with a broad range of substrates. At Centenary, my student collaborators and I are examining the use of these and related iron carbonyl compounds as perfluoroalkyl transfer reagents.