Novel Reagents and Catalysts for Organic Synthesis

用于有机合成的新型试剂和催化剂

基本信息

批准号：
10455044
负责人：
Shih-Yuan Liu
金额：
$ 32.87万
依托单位：
BOSTON COLLEGE
依托单位国家：
美国
项目类别：
财政年份：
2020
资助国家：
美国
起止时间：
2020-09-15 至 2024-07-31
项目状态：
已结题

项目摘要

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.

项目概要/摘要化学空间的生成及其转化为新功能是合成的主要目标之一化学。 BN/CC 等排（即用硼-氮键取代碳-碳键）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。该提案描述了 BN/CC 等排现象的一个尚未开发的新探索途径，即一个计划致力于开发芳烃的 BN 等排体作为有机合成的有用试剂和催化剂化学应用。研究这些 BN 杂环（也称为氮硼烷）的潜在好处包括发现使用传统有机化合物无法实现的新颖反应性和选择性化合物和新机械原理的发展，都是氮硼烷独特的结果电子结构。具体来说，我们力求： 1) 将氮杂硼烷建立为四碳（4C）+ 1氮（1N）+ 1硼（1B）合成子，用于合成应用利用氮硼烷的预装功能密度，即氮原子、硼原子和 1,3- 丁二烯装置可有效生产用于多样性合成的新型氨基硼化化合物。 2) 建立氮杂硼烷作为一个新的配体家族，可以与不同的配体进行不同的配位模式过渡金属影响金属催化转化中的新反应性和选择性。完成所提出的目标将产生新的易于获取和利用的试剂和催化剂系统可以完成现有方法不易实现的合成转化。