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功能化丙二腈的合成:烯烃的铁催化氢原子转移反应。

Synthesis of functionalized malononitriles Fe-catalysed hydrogen atom transfers of alkenes.

机构信息

Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.

Department of Orthopedic Surgery, Zhongda Hospital, School of Medicine, Southeast University, Nanjing, China.

出版信息

Org Biomol Chem. 2022 Feb 16;20(7):1480-1487. doi: 10.1039/d1ob02332b.

Abstract

Described herein is a practical and convenient approach that enabled radical-mediated conjugate addition of unreactive alkenes to electron-deficient alkenes leading to a broad range of substituted malononitriles. These reactions are believed to proceed by Fe-catalysed hydrogen atom transfer (HAT) onto the alkenes affording carbon-centered radical intermediates with Markovnikov selectivity, followed by the capture of electron-deficient alkenes. We explored this synthesis approach under mild conditions with high efficiency and broad substrate scope and the utility is highlighted by the further synthetic transformations of the obtained substituted malononitriles.

摘要

本文描述了一种实用且方便的方法,可实现自由基介导的缺电子烯烃与惰性烯烃的共轭加成,从而得到广泛的取代的丙二腈。这些反应被认为是通过 Fe 催化的氢原子转移(HAT)作用于烯烃,从而生成马氏选择性的碳中心自由基中间体,然后捕获缺电子烯烃。我们在温和的条件下以高效率和广泛的底物范围探索了这种合成方法,并通过进一步转化获得的取代的丙二腈突出了其应用价值。

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