Selective photooxygenations and oxidative C−H-functionalizations of indole alkaloids and polycyclic terpenes through quinone photoorganocatalysis

通过醌光有机催化选择性光氧化和吲哚生物碱和多环萜烯的氧化CâH功能化

• 批准号: 266793065
• 负责人: Professor Dr. Malte Brasholz
• 金额: --
• 依托单位: Institut für Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2014
• 资助国家: 德国
• 起止时间: 2013-12-31 至 2021-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/266793065?language=en
• 关键词: Selective; photooxygenations; oxidative; functionalizations; indole

The objective of this project is the application of catalytic photooxidations and photooxygenations to new selective transformations of tetrahydrocarbazoles, tetrahydro-β-carbolines, monoterpene indole alkaloids as well as betulin, a renewable chemical from the bark of the birch tree. Seminal previous investigations in the area of organic photocatalysis with quinones enable the guided selection and optimization of suitable catalysts and co-catalysts, to identify reaction conditions which are adjusted to the respective substrate classes investigated. The combination of photooxygenation reactions in conventional experimental setups with continuous flow reactors, which allow an efficient mass transfer between liquid and gas phase, enables accelerated and reproducible reaction optimization and the realization of high synthetic yields.

该项目的目标是应用催化光氧化和光氧化对四氢咔唑、四氢-β-咔啉、单萜吲哚生物碱以及桦木醇（一种来自桦树皮的可再生化学品）进行新的选择性转化。在醌类有机化合物领域的初步研究使得能够指导选择和优化合适的催化剂和助催化剂，以确定调整到相应底物类别的反应条件。在常规实验装置中的光氧化反应与连续流动反应器的组合允许液相和气相之间的有效传质，使得能够加速和可再现的反应优化并实现高合成产率。

项目成果

Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N‐Diacyliminium Ions

• DOI: 10.1002/anie.202007549
• 发表时间: 2020-06
• 期刊: Angewandte Chemie (International Ed. in English)
• 作者: Mario Frahm;T. Drathen;L. M. Gronbach;A. Voss;F. Lorenz;J. Bresien;A. Villinger;F. Hoffmann;M. Brasholz

Lewis Acid-Catalyzed Carbofunctionalization of Uncommon C,N-Diacyliminium Ions: Controlling Regio- and Enantioselectivity.

路易斯酸催化罕见 C,N-二酰亚胺离子的碳官能化：控制区域选择性和对映选择性

• DOI: 10.1021/acs.orglett.1c02857
• 发表时间: 2021
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: L. M. Gronbach;A. Voss;M. Frahm;A. Villinger;J. Bresien;D. Michalik;M. Brasholz
• 通讯作者: M. Brasholz