New Methods for the Synthesis of Biaryl Templates

该项目解决了一个模板集合的合成，可以用作快速合成一系列多取代双芳基的一般前体。通过传统的金属介导偶联方法不容易获得各种潜在有用的双芳基取代模式。这一缺点将通过Diels-Alder策略的发展来解决联芳基合成。联芳基合成的关键模板可通过易于获得的亲二烯试剂和氧化二烯获得。这种方法提供了环加成的原子经济效益和金属介导偶联合成双芳烯的效用之间的结合。有了这个奖项，有机和大分子化学项目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（类苯）环连接在一起的分子（双芳基）由于其在天然产物中作为结构基序的存在以及在金属催化中作为支持基团的效用而获得了相当大的合成兴趣。虽然已报道了构建选定的双芳基化合物的合成方法，但需要创新的策略来扩大其可及性。该项目的总体目标是合成一组模板，这些模板可作为快速合成一系列多取代双芳基的一般前体。而不是追求更传统的方法，涉及两个芳香环的耦合，卡特教授和他的学生正在开发合成路线，其中芳香环本身的结构。这为这类重要分子提供了一条潜在的通用和有效的合成途径。这一提议对合成新的药物靶点、手性配体和大分子结构的潜在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.