eEtherification: An Electrochemical Strategy toward the Synthesis of Sterically Hindered Dialkyl Ethers from Activated Alcohols

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-17 DOI:10.1021/acs.orglett.4c04093
Cyrille Kiaku, Simon Kaltenberger, Daniel Raydan, Valerio Morlacci, Bini Claringbold, Charles A. I. Goodall, Laura Palombi, Darren L. Poole, Kevin Lam
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Abstract

Traditional etherification methods, although staples in synthetic chemistry, often fall short in the efficient construction of sterically hindered dialkyl ethers, especially under mild and practical conditions. Recent advances have attempted to address these limitations, typically relying on transition metal catalysts, external reductants, or harsh reaction conditions. In this work, we disclose a novel electrochemical approach that enables the synthesis of sterically hindered ethers from economically relevant and readily accessible alcohols without the need for sacrificial oxidants. Our protocol exploits mild conditions to generate reactive carbocations, which are subsequently captured by alcohol nucleophiles to yield the desired ethers. This method is cost-effective, practical, and broad in scope, providing a valuable addition to chemists’ synthetic toolkit for ether synthesis.

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传统的醚化方法虽然是合成化学中的主要方法,但往往不能有效地构建立体受阻的二烷基醚,尤其是在温和而实用的条件下。最近的进展试图解决这些局限性,但通常依赖于过渡金属催化剂、外部还原剂或苛刻的反应条件。在这项工作中,我们揭示了一种新颖的电化学方法,这种方法能够从经济上相关且容易获得的醇中合成立体受阻醚,而无需牺牲氧化剂。我们的方案利用温和的条件生成反应性碳化物,然后由醇亲核物捕获生成所需的醚。这种方法成本低、实用性强、范围广,为化学家的醚合成工具包提供了宝贵的补充。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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