Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation
Zhiguo Zhao1, Yuanling Pang1, Ziqiang Zhao1
1School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry of the Ministry of Education, Shandong University, Jinan, 250100, China.
Nature Communications
|October 10, 2023
Summary
This study introduces a novel dual selenium bonding catalysis for activating ether C-O bonds. This approach overcomes challenges in supramolecular catalysis, enabling cyclization and coupling reactions.
Area of Science:
- Supramolecular Chemistry
- Organocatalysis
- Organic Synthesis
Background:
- Activating ether C-O bonds using weak interactions is a significant challenge in supramolecular catalysis.
- The strong C-O bond and deactivation of catalysts by ionic intermediates hinder progress.
Purpose of the Study:
- To develop a novel catalytic system for activating ether C-O bonds via weak interactions.
- To explore a new activation mode utilizing dual selenium bonding.
Main Methods:
- Employing a dual Se···π and Se···O bonding strategy for ether activation.
- Investigating the catalytic efficiency in cyclization, coupling, and elimination reactions.
Main Results:
- Successfully activated benzylic and allylic ether C-O σ-bonds using the dual selenium bonding approach.
- Demonstrated tolerance to various alkoxide leaving groups, outperforming other weak interaction donors.
Conclusions:
- The dual Se···π and Se···O bonding represents a distinctive and effective mode for supramolecular catalysis.
- This method offers a promising new avenue for ether C-O bond activation in organic synthesis.
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