This project addresses the synthesis of a collection of templates that can be employed as general precursors for the rapid synthesis of a range of polysubstituted biaryls. A variety of potentially useful substitution patterns for biaryls are not readily available via conventional metal-mediated coupling approaches. This shortcoming will be addressed through the development of a Diels-Alder strategy to biaryl synthesis. The key templates for biaryl synthesis are accessible via readily available dienophiles and oxygenated dienes. This approach provides a marriage between the atom-economical benefits of cycloadditions and the utility of metal-mediated couplings for the synthesis of biaryls.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Rich G. Carter of the Department of Chemistry at Oregon State University. Molecules containing two aromatic (benzene-like) rings linked together (biaryls) have garnered considerable synthetic interest due to their presence as a structural motif in natural products and their utility as supporting groups in metal catalysis. While synthetic methods have been reported for the construction of selected biaryls, innovative strategies are needed to broaden their accessibility. The overall goal of this project is to synthesize a collection of templates that can be employed as general precursors for the rapid synthesis of a range of polysubstituted biaryls. Rather than pursuing more conventional approaches, involving the coupling of two aromatic rings, Professor Carter and his students are developing synthetic routes in which the aromatic rings themselves are constructed. This affords a potentially general and efficient synthetic route to this important class of molecules. The potential wide-reaching impact of this proposal for the synthesis of new pharmaceutical targets, chiral ligands and macromolecular structures should have significant broad impact in the scientific community.
