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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
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Copper malonamide complexes and their use in azide-alkyne cycloaddition reactions
S J Bent1, M F Mahon, R L Webster
1Department of Chemistry, University of Bath, Claverton Down, Bath, UKBA2 7AY. r.l.webster@bath.ac.uk.
Dalton Transactions (Cambridge, England : 2003)
|May 12, 2015
Summary
Malonamide ligands were successfully used in copper catalysis for synthesizing oligo(triazoles) and organic azoles. This research highlights a novel application of malonamide in click chemistry and catalysis.
Area of Science:
- Coordination Chemistry
- Organic Synthesis
- Catalysis
Background:
- Malonamide derivatives are typically not explored as ligands in metal catalysis.
- Copper catalysis is a versatile tool for forming carbon-nitrogen bonds, particularly in click chemistry.
Purpose of the Study:
- To investigate the use of malonamide functionalities as O,O-chelating ligands in copper catalysis.
- To explore the application of these novel copper-malonamide complexes in organic synthesis, specifically in click chemistry reactions.
Main Methods:
- Synthesis and characterization of a homologous series of malonamide ligands.
- Complexation of these ligands with copper.
- Structural investigation of the resulting copper-malonamide complexes.
- Application of the complexes in azide-alkyne cycloaddition reactions.
Main Results:
- Successfully ligated malonamide derivatives to copper, forming novel O,O-chelating architectures.
- Characterized the structure of these copper-malonamide complexes.
- Demonstrated the efficacy of these complexes in catalyzing azide-alkyne cycloaddition reactions.
- Achieved step-growth synthesis of oligo(triazoles) and synthesis of small organic azoles.
Conclusions:
- Malonamide functionality represents a rare and effective ligand class in copper catalysis.
- The developed copper-malonamide catalytic systems are suitable for the synthesis of oligo(triazoles) and other organic azoles.
- This work expands the scope of ligands used in copper-catalyzed click chemistry.
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