New Methods for the Synthesis of Biaryl Templates

该项目涉及一系列模板的合成，这些模板可用作快速合成一系列多取代联芳基的一般前体。通过传统的金属介导的偶联方法，联芳基的各种潜在有用的取代模式并不容易获得。这一缺点将通过开发Diels-Alder策略来进行联芳基合成来解决。用于联芳基合成的关键模板可以通过现成的亲二烯烃和含氧二烯来获得。这种方法将环加成反应的原子经济性和金属介导型偶合反应在合成联芳烃中的效用结合在一起。有了这个奖项，有机和高分子化学计划将支持俄勒冈州立大学化学系的Rich G.Carter博士的研究。含有两个芳香族(苯环)相连(联芳基)的分子由于在天然产物中作为结构基元的存在和在金属催化中作为支撑基的应用而引起了人们的极大兴趣。虽然已经报道了用于构建选定的联芳基的合成方法，但需要创新的战略来扩大它们的可及性。该项目的总体目标是合成一系列模板，这些模板可用作快速合成一系列多取代联芳基的一般前体。卡特教授和他的学生没有追求更传统的方法，包括两个芳香环的偶联，而是开发了构建芳香环本身的合成路线。这为这类重要的分子提供了一条潜在的通用而有效的合成路线。这一提议对合成新的药物靶标、手性配体和大分子结构具有潜在的广泛影响，应该在科学界产生重大的广泛影响。

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.