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Updated: May 25, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Apical functionalization of chiral heterohelicenes
Sravan K Surampudi1, G Nagarjuna, Daiki Okamoto
1Department of Chemistry, University of Massachusetts Amherst, 710 North Pleasant Street, Amherst, Massachusetts 01003, USA.
Researchers developed a new copper-catalyzed amination method for selectively functionalizing chiral bridged triarylamines. This regioselective synthesis enables the creation of complex molecules, including chiral heterohelicene homodimers.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Chiral bridged triarylamines are important molecular scaffolds.
- Selective functionalization of complex organic molecules remains a challenge.
Purpose of the Study:
- To develop a regioselective synthetic protocol for functionalizing chiral bridged triarylamines.
- To demonstrate the utility of this method in synthesizing complex chiral structures.
Main Methods:
- Copper-catalyzed amination reaction for selective C-N bond formation.
- Utilizing differential reactivity of aryl-Br bonds based on steric and electronic properties.
- Stille coupling for subsequent molecular assembly.
Main Results:
- Selective functionalization of the apical position of chiral bridged triarylamines achieved.
- Successful coupling of diphenylamines with sterically hindered, electronically activated aryl-Br bonds.
- Synthesis of a chiral heterohelicene homodimer via Stille coupling.
Conclusions:
- The developed protocol offers a precise method for regioselective functionalization.
- This approach expands synthetic possibilities for complex chiral molecules.
- The strategy is effective for constructing advanced molecular architectures.
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