Photoinduced Pd-Catalyzed Carbonylative Formal [2 + 2] Cycloaddition of Alkylarenes and Imines

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-29 DOI:10.1021/acs.orglett.5c03465

Yi-Cong Liu, Wen-Ao Li, Mostafa Sayed, Zhi-Yong Han, Liu-Zhu Gong

引用次数: 0

Abstract

A photoinduced palladium-catalyzed carbonylative formal [2 + 2] cycloaddition of toluene derivatives and imines provides a direct access to β-lactams under mild conditions (35 °C, 455 nm LED, 2 bar CO) with up to 99% yields. This three-component reaction accommodates both aldimines and ketimines as well as diverse aryl substrates, including ethylbenzene derivatives. Mechanistic studies reveal a sequential process consisting of C–H bond activation, carbonylation, and in situ ketene formation. This atom-economical protocol offers a valuable synthetic route to pharmaceutically important β-lactam scaffolds directly from readily available starting materials.

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光诱导pd催化烷基烯和亚胺羰基化形式[2 + 2]环加成

光诱导钯催化甲苯衍生物和亚胺的羰基化形式[2 + 2]环加成在温和条件下（35°C, 455nm LED, 2 bar CO）可直接获得β-内酰胺，收率高达99%。这个三组分反应可容纳醛胺和酮胺以及各种芳基底物，包括乙苯衍生物。机理研究揭示了一个由C-H键激活、羰基化和原位烯酮形成组成的连续过程。这种原子经济的方案提供了一条有价值的合成途径，可以直接从现成的起始材料中合成具有重要药用价值的β-内酰胺支架。

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.