Cu-Catalyzed Hydrodechlorination of Unactivated Alkyl Chlorides Using Diisobutylaluminum Hydride

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-11-12 DOI:10.1021/acs.orglett.4c03774
Subin Yoon, Seeun Lim, Soohong Cho, Yunmi Lee
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Abstract

A copper-catalyzed hydrodechlorination of primary, secondary, and tertiary alkyl chlorides using diisobutylaluminum hydride is reported. This catalytic system offers a broad substrate scope, high yields, and good functional group tolerance. Mechanistic investigations indicated that the reaction predominantly proceeds via a radical pathway, as supported by radical clock experiments. Importantly, this study provides a new approach for the selective hydrodechlorination of unactivated alkyl chlorides and expands the utility of Cu-hydride catalysis in sustainable chemical synthesis.

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铜催化二异丁基氢化铝对未活化烷基氯的加氢脱氯反应
报告了一种使用二异丁基氢化铝对伯、仲和叔烷基氯进行铜催化加氢脱氯的方法。这种催化体系具有广泛的底物范围、高产率和良好的官能团耐受性。机理研究表明,该反应主要通过自由基途径进行,自由基时钟实验也证明了这一点。重要的是,这项研究为未活化烷基氯的选择性加氢脱氯提供了一种新方法,并拓展了铜酸酐催化在可持续化学合成中的应用。
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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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