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A biaryl cross-coupling strategy for functionalisation of benzocrown ethers
Sally Dixon1, Richard C D Brown, Philip A Gale
1School of Chemistry, University of Southampton, Highfield, Southampton, Hampshire, UK.
Novel crown ether systems were synthesized using palladium-catalyzed cross-coupling reactions. This method efficiently prepares (di)benzocrown-substituted aryl-zinc or -boron reagents with functionalized aryl halides.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Crown ethers are macrocyclic polyethers with significant applications in ion binding and host-guest chemistry.
- Developing efficient synthetic routes to novel crown ether derivatives is crucial for expanding their utility.
Purpose of the Study:
- To describe a convenient method for synthesizing novel crown ether systems.
- To utilize palladium-catalyzed cross-coupling reactions for this purpose.
Main Methods:
- Preparation of (di)benzocrown-substituted aryl-zinc reagents.
- Preparation of (di)benzocrown-substituted aryl-boron reagents.
- Palladium-catalyzed cross-coupling reactions with functionalized aryl halides.
Main Results:
- Successful synthesis of novel (di)benzocrown-substituted aryl-zinc and aryl-boron reagents.
- Efficient palladium-catalyzed cross-coupling of these reagents with aryl halides.
- Demonstration of a convenient route to novel crown ether systems.
Conclusions:
- The described palladium-catalyzed cross-coupling strategy provides a facile and efficient method for constructing complex crown ether architectures.
- This approach broadens the scope of accessible crown ether derivatives for various applications.
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