铜催化未活化烯烃与溴代烷烃的双官能团化/环化反应
Copper-Catalyzed Bifunctionalization/Annulation of Unactivated Alkene with Alkyl Bromides.
作者信息
Feng Cancan, Wu Yangjie
机构信息
College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.
出版信息
J Org Chem. 2023 Nov 3;88(21):15249-15255. doi: 10.1021/acs.joc.3c01746. Epub 2023 Oct 20.
β-Lactam is a ubiquitous scaffold in bioactive compounds and pharmaceuticals. Herein, we disclose a streamlined method for the construction of β-lactams starting from unactivated alkenes and alkyl bromides via a Cu-catalyzed inter-/intramolecular carboamidation. This reaction proceeded smoothly under mild reaction conditions and exhibited a broad substrate scope and various functional groups. This protocol is not only compatible with 1, 2, and 3° alkyl bromides but also suitable for α-bromo nitrile as well as various benzyl bromides. The mechanism exploration indicated that sequential radical addition/reductive elimination was involved.
β-内酰胺是生物活性化合物和药物中普遍存在的骨架。在此，我们公开了一种从未活化的烯烃和烷基溴出发，通过铜催化的分子间/分子内碳酰胺化反应构建β-内酰胺的简化方法。该反应在温和的反应条件下顺利进行，底物范围广泛，适用于各种官能团。该方法不仅与伯、仲、叔烷基溴兼容，还适用于α-溴代腈以及各种苄基溴。机理研究表明，该反应涉及自由基的顺序加成/还原消除过程。
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