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Updated: Jul 16, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of densely functionalised arenes using [2 + 2 + 2] cycloaddition reactions
Jonathan Clayden1, Wesley J Moran
1School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK. clayden@man.ac.uk
Rhodium(I)-catalyzed cycloaddition synthesizes sterically hindered aryl ethers and diarylmethanes from simple alkynes. The resulting diarylmethanes did not exhibit rotational restriction in NMR spectra.
Area of Science:
- Organic Chemistry
- Organometallic Chemistry
- Catalysis
Background:
- Cycloaddition reactions are fundamental in organic synthesis.
- Rhodium catalysis offers unique pathways for C-C bond formation.
- Steric hindrance presents challenges in synthesizing complex molecules.
Purpose of the Study:
- To develop a Rh(I)-catalyzed [2+2+2] cycloaddition method.
- To synthesize sterically hindered aryl ethers and diarylmethanes.
- To investigate the structural properties of the synthesized diarylmethanes.
Main Methods:
- Utilizing rhodium(I) catalysts for [2+2+2] cycloaddition reactions.
- Employing diyne and alkyne precursors.
- Characterization of products using Nuclear Magnetic Resonance (NMR) spectroscopy.
Main Results:
- Successful synthesis of aryl ethers and diarylmethanes with significant steric hindrance.
- The synthesized diarylmethanes showed no evidence of rotational restriction in their NMR spectra.
- Demonstrated the utility of Rh(I)-catalysed cycloaddition for constructing sterically demanding structures.
Conclusions:
- Rh(I)-catalyzed [2+2+2] cycloaddition is an effective route to sterically hindered aryl ethers and diarylmethanes.
- The lack of observed rotational restriction in diarylmethanes warrants further investigation.
- This method provides access to complex molecular architectures from simple starting materials.
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