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Crossover-Annulation/Oxygenation Approach to Functionalized Phenanthridines by Palladium-Copper Relay Catalysis
Xiang Liu1, Renjie Mao1, Cheng Ma1
1Department of Chemistry, Zhejiang University , 20 Yugu Road, Hangzhou 310027, China.
Organic Letters
|November 28, 2017
Summary
Researchers developed a new palladium-copper catalyzed reaction. This process efficiently synthesizes complex 9-acylphenanthridine compounds from simple starting materials.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Phenanthridine derivatives are important scaffolds in medicinal chemistry.
- Efficient synthetic routes to substituted phenanthridines are highly sought after.
- Tandem reactions offer streamlined access to complex molecular architectures.
Purpose of the Study:
- To develop a novel tandem reaction for the synthesis of 9-acylphenanthridine compounds.
- To explore the utility of palladium-copper relay catalysis in a three-component coupling reaction.
- To establish a new method for constructing highly functionalized phenanthridine cores.
Main Methods:
- A tandem crossover-annulation and oxygenation strategy was employed.
- Conjugated enediyne-acids and ortho-alkynylanilines were used as substrates.
- Palladium-copper relay catalysis was utilized under an oxygen atmosphere.
Main Results:
- The reaction successfully achieved a three-component assembly of 9-acylphenanthridine compounds.
- The process demonstrated high efficiency and functional group tolerance.
- This method provides a novel route to valuable phenanthridine derivatives.
Conclusions:
- A novel and efficient tandem crossover-annulation and oxygenation process was established.
- Palladium-copper relay catalysis enables the facile synthesis of 9-acylphenanthridines.
- This methodology offers a valuable tool for accessing complex phenanthridine structures.
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