直接自由基官能化方法构建取代的金刚烷和类金刚石。
Direct radical functionalization methods to access substituted adamantanes and diamondoids.
机构信息
Chemistry, University of Iowa, Iow City, Iowa, USA.
University of California Riverside, Riverside, California, USA.
出版信息
Org Biomol Chem. 2021 Dec 22;20(1):10-36. doi: 10.1039/d1ob01916c.
Adamantane derivatives have diverse applications in the fields of medicinal chemistry, catalyst development and nanomaterials, owing to their unique structural, biological and stimulus-responsive properties, among others. The synthesis of substituted adamantanes and substituted higher diamondoids is frequently achieved carbocation or radical intermediates that have unique stability and reactivity when compared to simple hydrocarbon derivatives. In this review, we discuss the wide range of radical-based functionalization reactions that directly convert diamondoid C-H bonds to C-C bonds, providing a variety of products incorporating diverse functional groups (alkenes, alkynes, arenes, carbonyl groups, .). Recent advances in the area of selective C-H functionalization are highlighted with an emphasis on the H-atom abstracting species and their ability to activate the particularly strong C-H bonds that are characteristic of these caged hydrocarbons, providing insights that can be applied to the C-H functionalization of other substrate classes.
金刚烷衍生物因其独特的结构、生物和刺激响应特性等，在药物化学、催化剂开发和纳米材料等领域有广泛的应用。取代金刚烷和取代高金刚烷的合成通常是通过碳阳离子或自由基中间体来实现的，与简单的碳氢化合物衍生物相比，它们具有独特的稳定性和反应活性。在这篇综述中，我们讨论了广泛的基于自由基的官能团化反应，这些反应可以直接将金刚烷 C-H 键转化为 C-C 键，提供了各种包含不同官能团（烯烃、炔烃、芳烃、羰基等）的产物。我们强调了选择性 C-H 官能化方面的最新进展，重点介绍了能够激活这些笼状碳氢化合物特征的特别强的 C-H 键的 H 原子提取物种，以及它们在应用于其他底物类别的 C-H 官能化方面的应用潜力。
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