Catalytic and medicinal chemistry of novel boron-fluorine functionalized drug-like molecules

Alexis Ravenscroft*, Randika Abeysinghe, Mason Hamilton, and Brian Popp
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506

Presentation No.: 110

Assigned Category (Presentation Format): Physical Sciences (Poster Presentations)

Student’s Major: Chemistry

Boron-containing compounds are a commonality in organic chemistry and are fundamental, especially for Suzuki-Miyaura cross coupling. Trifuoroborates have had some studies in the research community, however, difluoroborates have not had as much synthesis attention. Difluoroboralactonates are in a category all on their own, yet to be analyzed and tested and their potential is completely unknown. While synthesizing the compound, the generality of the reaction and the methodology were studied in attempt to optimize the reaction. This was done by working with different solvents, varied substrates and multiple purification methods to find the optimal combination. NMR spectroscopy was used to analyzing and characterizing the product to affirm the presence of the desired compound. After verifying the compound, the next part of the experiment focused on the common, Nobel prize-winning Suzuki Cross-coupling reaction with an aryl electrophile. Preliminary catalytic results show the expected disappearance of the difluoroboron moeity and introduction of a new carbon-aryl bond forming the 2,3-diarylpropionic acid.

Funding: NSF Career: CHE-1752986

Program/mechanism supporting research/creative efforts: WVU's SURE program (Rita Rio & Michelle Richards-Babb)