Photocatalytic Diheteroarylation of [1.1.1]Propellane for the Construction of 1,3-Diheteroaryl Bicyclo[1.1.1]pentanes

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-23 DOI:10.1021/acs.orglett.4c0319810.1021/acs.orglett.4c03198

Guoxiang Bao, Yue Wang, Wenhao Xu, Zhihao Yu, Wei Zhou, Jiacheng Li, Longyi Li and Xinpeng Jiang*,

引用次数: 0

Abstract

Herein, we report a visible light-induced diheteroarylation reaction of [1.1.1]propellane to synthesize 1,3-diheteroaryl bicyclo[1.1.1]pentanes (BCPs). In this approach, heteroaryl radicals are generated from heteroaryl halides via photocatalysis and subsequently added to [1.1.1]propellane. The in situ generated BCP radicals are then trapped by various heterocycles to furnish 1,3-diheteroaryl BCPs. Notably, this strategy features metal-free, mild conditions and utilizes inexpensive catalyst. For the first time, the diheteroarylation of [1.1.1]propellane could be achieved via a radical strategy, allowing for the efficient synthesis of 1,3-diheteroaryl BCPs with various applications in organic and medicinal chemistry.

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光催化[1.1.1]丙环烷的二硬脂酰化作用以构建 1,3-二硬脂酰基双环[1.1.1]戊烷

在此，我们报告了一种可见光诱导的 [1.1.1]propellane 二杂芳基化反应，用于合成 1,3- 二杂芳基双环[1.1.1]戊烷 (BCPs)。在这种方法中，杂芳基自由基通过光催化从杂芳基卤化物中生成，然后加入到[1.1.1]丙烷中。然后，原位生成的 BCP 自由基被各种杂环捕获，生成 1,3-二杂芳基 BCP。值得注意的是，这种方法不含金属，条件温和，使用的催化剂价格低廉。这是首次通过自由基策略实现[1.1.1]丙烷的二硬脂酰化，从而高效合成 1,3-二硬脂酰基 BCPs，并将其广泛应用于有机化学和药物化学领域。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.