eEtherification:\nAn Electrochemical Strategy toward\nthe Synthesis of Sterically Hindered Dialkyl Ethers from Activated\nAlcohols

Traditional etherification methods, although staples\nin synthetic\nchemistry, often fall short in the efficient construction of sterically\nhindered dialkyl ethers, especially under mild and practical conditions.\nRecent advances have attempted to address these limitations, typically\nrelying on transition metal catalysts, external reductants, or harsh\nreaction conditions. In this work, we disclose a novel electrochemical\napproach that enables the synthesis of sterically hindered ethers\nfrom economically relevant and readily accessible alcohols without\nthe need for sacrificial oxidants. Our protocol exploits mild conditions\nto generate reactive carbocations, which are subsequently captured\nby alcohol nucleophiles to yield the desired ethers. This method is\ncost-effective, practical, and broad in scope, providing a valuable\naddition to chemists’ synthetic toolkit for ether synthesis.

Publication Details

Journal
Figshare
Published
2024-12-17
DOI
https://doi.org/10.1021/acs.orglett.4c04093.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

eEtherification:\nAn Electrochemical Strategy toward\nthe Synthesis of Sterically Hindered Dialkyl Ethers from Activated\nAlcohols

Figshare
Radical Photochemical Reactions
article

eEtherification:\nAn Electrochemical Strategy toward\nthe Synthesis of Sterically Hindered Dialkyl Ethers from Activated\nAlcohols

article en

Abstract

Traditional etherification methods, although staples\nin synthetic\nchemistry, often fall short in the efficient construction of sterically\nhindered dialkyl ethers, especially under mild and practical conditions.\nRecent advances have attempted to address these limitations, typically\nrelying on transition metal catalysts, external reductants, or harsh\nreaction conditions. In this work, we disclose a novel electrochemical\napproach that enables the synthesis of sterically hindered ethers\nfrom economically relevant and readily accessible alcohols without\nthe need for sacrificial oxidants. Our protocol exploits mild conditions\nto generate reactive carbocations, which are subsequently captured\nby alcohol nucleophiles to yield the desired ethers. This method is\ncost-effective, practical, and broad in scope, providing a valuable\naddition to chemists’ synthetic toolkit for ether synthesis.

Figshare
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Radical Photochemical Reactions
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