Ring-closing C–O/C–O metathesis of ethers with primary aliphatic alcohols

Hongmei Liu, Qing Huang, Rong-zhen Liao, Man Li () and Youwei Xie ()
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Hongmei Liu: Huazhong University of Science and Technology
Qing Huang: Huazhong University of Science and Technology
Rong-zhen Liao: Huazhong University of Science and Technology
Man Li: Huazhong University of Science and Technology
Youwei Xie: Huazhong University of Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract In canonical organic chemistry textbooks, the widely adopted mechanism for the classic transetherifications between ethers and alcohols starts with the activation of the ether in order to weaken the C–O bond, followed by the nucleophilic attack by the alcohol hydroxy group, resulting in a net C–O/O–H σ-bond metathesis. In this manuscript, our experimental and computational investigation of a Re2O7 mediated ring-closing transetherification challenges the fundamental tenets of the traditional transetherification mechanism. Instead of ether activation, the alternative activation of the hydroxy group followed by nucleophilic attack of ether is realized by commercially available Re2O7 through the formation of perrhenate ester intermediate in hexafluoroisopropanol (HFIP), which results in an unusual C–O/C–O σ-bond metathesis. Due to the preference for the activation of alcohol rather than ether, this intramolecular transetherification reaction is therefore suitable for substrates bearing multiple ether moieties, unparalleled by any previous methods.

Date: 2023
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DOI: 10.1038/s41467-023-37538-1

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