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

• 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

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.

芳香化合物在科学和共同环境的各个方面（例如自然和智能材料）都起着领导作用。因此，该提案试图将炔烃的Ni催化性环加成作为合成的有效和原子经济方法，这些方法是合成强大的成分，用于形成芳族和类似的杂环化合物。该过程的显着优势是使用相对简单的起始材料，这些起始材料允许构建复杂且重大取代的结构。优先地，应使用供体功能化的炔烃建立Ni-catalysed苯并苯二苯甲酸的反应机制。借助这些机械洞察力，应设计横向选择性高水平的底物。此步骤将是NI催化苯甲酸的关键里程碑。在本文中，Ni-catalysed反应的可用工具箱应大大扩展为芳香族和模拟杂环硼酸盐（例如，含有氮或氧气的羰基化合物）尚未通过过渡金属猫的疾病制备。由于它们的歧管下游化学，特定的重点将放在无法使用当前方法访问的多环化合物上。

项目成果

Investigation of alkyne regioselectivity in the ni-catalyzed benzannulation of cyclobutenones.

• DOI: 10.1002/chem.201405863
• 发表时间: 2015-02
• 期刊: Chemistry
• 作者: T. Stalling;W. Harker;A. Auvinet;E. J. Cornel;J. Harrity