Novel Reagents and Catalysts for Organic Synthesis

项目摘要/摘要 化学空间的生成及其向新功能的转化是人工合成的主要目标之一 化学反应。BN/CC等构体(即，用硼-氮键取代碳-碳键)具有 成为增加与生物医学研究相关的化合物的化学空间的可行策略。 这项提议描述了一种尚未开发的探索BN/CC等位作用的新途径，即一个程序 发展芳烃BN异构体作为合成有机的有用试剂和催化剂 化学应用。研究这些BN杂环(也称为氮硼化合物)的潜在益处 包括发现通过使用传统有机物质无法获得新的反应性和选择性 化合物和新的机械原理的发展，都是由于氮博林的独特 电子结构。 具体地说，我们力求： 1)建立四碳(4C)+一氮(1N)+一硼(1B)合成子用于合成应用 其利用了氮硼的预先设置的官能团密度，即氮原子、硼原子和1，3- 丁二烯装置高效地生产新的氨基硼化化合物，用于面向多样性的合成。 2)将氮硼化合物建立为一种新的配体家族，可以与 过渡金属在金属催化转化中影响新的反应性和选择性。 完成拟议的目标将产生新的易于获取和使用的试剂和催化剂系统 这可以完成现有方法难以实现的合成变换。

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.