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Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation

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  • Zhiguo Zhao

    (Shandong University)

  • Yuanling Pang

    (Shandong University)

  • Ziqiang Zhao

    (Shandong University)

  • Pan-Pan Zhou

    (Lanzhou University)

  • Yao Wang

    (Shandong University)

Abstract

The activation of ethers by weak interactions is a long-standing objective in supramolecular catalysis, but yet it remains an underdeveloped topic. The obstacles towards solving this problem are prominent since it is difficult for a weak interaction to cleave a relatively strong C-O σ-bond and moreover, the ionic intermediate composing of an alkoxide ion and an electrophilic carbocation would deactivate weak interaction donors. Herein, we describe a distinctive activation mode, dual Se···π and Se···O bonding, that could activate benzylic as well as allylic ether C-O σ-bonds to achieve cyclization, coupling and elimination reactions. This dual Se···π and Se···O bonding catalysis approach could tolerate various alkoxide leaving groups, while the other representative weak interaction donors showed no catalytic activity.

Suggested Citation

  • Zhiguo Zhao & Yuanling Pang & Ziqiang Zhao & Pan-Pan Zhou & Yao Wang, 2023. "Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42129-1
    DOI: 10.1038/s41467-023-42129-1
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