苄醇与烷烃和醛对 [1.1.1]Propellane 的官能化作用

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-21 DOI:10.1021/acs.orglett.4c03429

Fei Li, Jianyang Dong, Chenya Wang, Huijuan Liao, Jiayi Dang, Juan Zhou, Gang Li, Dong Xue

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引用次数: 0

摘要

双环[1.1.1]戊烷（BCPs）作为富含 C(sp3) 的苯环生物异构体，在药物发现研究中发挥着至关重要的作用。然而，迄今为止，具有强烷烃 C(sp3)-H 键的 BCPs 的制备方法尚未见报道。在本研究中，我们报告了一种在无金属和光催化剂条件下，用脂肪族碳氢化合物（以前从未为此进行过探索）和醛类对 [1.1.1]propellane 进行光诱导苄醇官能化的方法。BCP 产物可转化为各种有用的衍生物，证明了该方法的实用性。值得注意的是，我们实现了用简单烷烃合成功能化 BCP。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Benzyl Alcohol Functionalization of [1.1.1]Propellane with Alkanes and Aldehydes

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Benzyl Alcohol Functionalization of [1.1.1]Propellane with Alkanes and Aldehydes

Bicyclo[1.1.1]pentanes (BCPs) play a crucial role in drug discovery research as C(sp³)-rich bioisosteres of benzene rings. However, the preparation of BCPs with strong alkane C(sp³)–H bonds has not been reported to date. In this study, we reported a method for light-induced benzyl alcohol functionalization of [1.1.1]propellane with aliphatic hydrocarbons (which have not previously been explored for this purpose) and aldehydes under metal- and photocatalyst-free conditions. The BCP products could be transformed into various useful derivatives, demonstrating the utility of the method. Notably, we achieved the synthesis of functionalized BCPs with simple alkanes.

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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.