Our Research
Fluorination Methodology
Fluorine is an incredibly powerful and versatile element. The incorporation of fluorine into a potential drug target can influence that molecule's acidity, conformation, lipophilicity and metabolic stability. However, installing fluorine atoms into specific positions remains a significant challenge.
Our fluorination work aims at creating improved reagents for deoxyfluorination methodologies. Key considerations for these new reagents were: 1) efficiency, 2) ease of use and 3) tunability. To this end, we have created novel sulfone iminium fluorides (SIFs) which convert alcohols to alkyl fluorides in less than 60 seconds, achieving the fastest fluorination rates to date. We have also expanded the use of these SIFs to synthesize valuable acyl fluorides from carboxylic acids as well as new connectors in Sulfur Fluoride Exchange (SuFEx) chemistry.
Current efforts on this project are centered on expanding the usage of these highly reactive SIF reagents.
See our recent publications on this topic:
Vogel, J. A.; Hammami, R.; Ko, A.; Datta, H.; Eiben, Y. N.; Labenne, K. J.; McCarver, E. C.; Yilmaz, E. Z.; Melvin, P. R. Org. Lett. 2022, 24, 5962.
Miller, L. P.; Vogel, J. A.; Harel, S.; Krussman, J. M.; Melvin, P. R. Org. Lett. 2023, 25, 1834.
Ancillary Ligand Design
The application of organometallic catalysts to organic transformations has forever altered the way we view synthetic challenges. Ancillary ligands have played a significant role in facilitating this development by imparting key stereo-electronic properties onto the metal center.
Our laboratory studies a novel class of ancillary ligands: carbodicarbenes (CDCs). These ligands have tremendous sigma-donating power and therefore could open the door to new and exciting organic transformations. Current work focuses on the synthesis of palladium and nickel complexes bearing bidentate CDC / phosphine ligands to be used in challenging cross-coupling reactions.
