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Superbase-promoted selective carbon-carbon bond cleavage driven by aromatization
Can Liu1, Xianjin Zhu2, Yongzhen Han2
1School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, P. R. China. fuhua@mail.tsinghua.edu.cn and Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Organic & Biomolecular Chemistry
|May 9, 2019
Summary
A new copper-catalyzed reaction cleaves carbon-carbon bonds in imine hydrochlorides, forming fused N-heterocycles. Aromatization and a superbase drive this novel chemical transformation for creating biologically active indoloquinolines.
Area of Science:
- Organic Chemistry
- Heterocyclic Chemistry
- Catalysis
Background:
- Carbon-carbon single bond cleavage is a fundamental transformation in organic synthesis.
- Developing selective methods for C-C bond cleavage remains a significant challenge.
- Fused N-heterocycles, such as indoloquinolines, exhibit diverse biological activities.
Purpose of the Study:
- To disclose a novel selective carbon-carbon single bond cleavage reaction.
- To synthesize fused N-heterocycles, specifically indoloquinoline derivatives.
- To elucidate the mechanism underlying the observed C-C bond cleavage.
Main Methods:
- Copper-catalyzed reaction between 1-alkyl-3-alkylindolin-2-imine hydrochlorides and substituted 1-(bromomethyl)-2-iodobenzenes.
- Mechanistic studies involving analysis of reaction intermediates and driving forces.
- Synthesis and characterization of the resulting fused N-heterocycles.
Main Results:
- A novel selective carbon-carbon single bond cleavage was achieved.
- Fused N-heterocycles, identified as indoloquinoline derivatives, were successfully synthesized.
- Mechanistic investigations revealed aromatization and superbase action as key factors for C-C bond cleavage.
Conclusions:
- The developed copper-catalyzed reaction provides an efficient route to fused N-heterocycles.
- The study highlights the importance of aromatization and superbase-mediated processes in C-C bond cleavage.
- The synthesized indoloquinoline derivatives possess potential for wide biological applications.
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