Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation

Zhiguo Zhao, Yuanling Pang, Ziqiang Zhao, Pan-Pan Zhou and Yao Wang ()
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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

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-42129-1

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