Novel Reagents and Catalysts for Organic Synthesis

项目总结/摘要 化学空间的产生及其转化为新的功能是合成的主要目标之一 化学. BN/CC电子等排性（即，用硼-氮键取代碳-碳键）具有 作为一种可行的策略，以增加与生物医学研究相关的化合物的化学空间。 该建议描述了BN/CC电子等排的一种新的未开发的探索途径，即程序 致力于开发芳烃的BN电子等排体作为合成有机化合物的有用试剂和催化剂， 化学应用研究这些BN杂环（也称为氮杂硼杂环）的潜在益处 包括发现了通过使用常规有机溶剂不能达到新的反应性和选择性 化合物和新的机械原理的发展，都是由于氮杂硼的独特的 电子结构 具体而言，我们力求： 1)建立用于合成应用四碳（4C）+1氮（1 N）+1硼（1B）合成子 其利用氮杂硼的预先安装的功能密度，即，氮原子、硼原子和1，3- 丁二烯单元，以有效地产生用于多样性定向合成的新的氨基硼化化合物。 2)建立了氮杂硼杂环作为新的配体家族，其可以与 过渡金属在金属催化的转化中影响新的反应性和选择性。 完成所提出的目标将产生新的容易获得和利用的试剂和催化剂体系 其可以完成现有方法不容易实现的合成转化。

Project Summary/Abstract The generation of chemical space and its translation into new functions is one of the main goals of synthetic chemistry. The BN/CC isosterism (i.e., replacement of a carbon-carbon bond with a boron-nitrogen bond) has emerged as a viable strategy to increase the chemical space of compounds relevant to biomedical research. This proposal describes a new untapped avenue of exploration for BN/CC isosterism, namely a program geared toward developing BN isosteres of arenes as useful reagents and catalysts for synthetic organic chemistry applications. Potential benefits of research into these BN heterocycles (also known as azaborines) include discovery of novel reactivity and selectivity that are unattainable by using conventional organic compounds and the development of new mechanistic principles, both as a consequence of azaborine's unique electronic structure. Specifically, we seek to: 1) establish azaborines as four-carbon (4C) + 1 nitrogen (1N) + 1 boron (1B) synthon for synthetic applications that exploit the preinstalled functional density of an azaborine, i.e., a nitrogen atom, a boron atom, and a 1,3- butadiene unit to efficiently produce new aminoborylated compounds for diversity-oriented synthesis. 2) establish azaborines as a new family of ligands that can engage in distinct coordination modes with transition metals to affect new reactivity and selectivity in metal-catalyzed transformations. Completion of the proposed aims will yield new readily accessible and utilizable reagents and catalyst systems that can accomplish synthetic transformations not readily achievable by existing methods.