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Synthetic and Mechanistic Studies on Ni-catalysed Benzannulation Reactions

Ni催化苯环化反应的合成及机理研究

基本信息

批准号：
250786160
负责人：
Dr. Timo Stalling
金额：
--
依托单位：
Department of Chemistry
依托单位国家：
德国
项目类别：
Research Fellowships
财政年份：
2013
资助国家：
德国
起止时间：
2012-12-31 至 2013-12-31
项目状态：
已结题

来源：
https://gepris.dfg.de/gepris/projekt/250786160?language=en
关键词：
Synthetic Mechanistic Studies Ni catalysed

项目摘要

Aromatic compounds play a leading role in all aspects of the scientific and common environment (e.g. natural and smart materials). Therefore, this proposal seeks to grow Ni-catalysed cycloadditions of alkynes as an efficient and atom economic method for the synthesis of boronates, which are synthetically powerful components for the formation of aromatic and analogous heterocyclic compounds. The remarkable advantage of this process is the use of relatively simple starting materials which allow to construct complex and heavily substituted structures.Predominantly, the reaction mechanism of the Ni-catalysed benzannulation of cyclobutenones should be established by using donor functionalized alkynes. With these mechanistic insights, substrates that offer consistently high levels of regioselectively in the benzannulation reaction should be designed. This step would be a key milestone for Ni-catalysed benzannulation.Finally, the available toolbox of Ni-catalysed reactions should be significantly expanded to aromatic and analog heterocyclic boronates (e. g. carbonyl compounds containing nitrogen or oxygen) which have not yet been prepared by transition metal catalysis. Due to their manifold downstream chemistry a particular focus will be on the preparation of polycyclic compounds that cannot be accessed using the current methodology.

芳香族化合物在科学和公共环境(如天然和智能材料)的各个方面都发挥着主导作用。因此，这项建议旨在将镍催化的炔环加成反应作为合成硼酸盐的一种有效且原子经济的方法，而硼酸盐是合成芳香族化合物和类似杂环化合物的有效成分。该方法的显著优点是使用相对简单的起始原料，可以构建复杂的和大量取代的结构。主要的是，镍催化的环丁烯酮的苯环化反应机理应该通过使用给体功能化的炔烃来建立。有了这些机理上的见解，应该设计出在苯环化反应中提供持续高水平区域选择性的底物。这一步骤将是镍催化苯甲化反应的一个关键里程碑。最后，现有的镍催化反应工具箱应显著扩展到尚未通过过渡金属催化制备的芳香族和类似杂环硼酸盐(如含氮或氧的羰基化合物)。由于多环化合物具有多种下游化学成分，因此将特别侧重于用目前的方法无法获得的多环化合物的制备。