The oxidation of unactivated C–H bonds has emerged as an effective tactic in natural product synthesis and has altered how chemists approach the synthesis of complex molecules. The use of C–H oxidation methods has simplified the process of synthesis planning by expanding the choice of starting materials, limiting functional group interconversion and protecting group manipulations, and enabling late-stage diversification. In this Review, we propose classifications for C–H oxidations on the basis of their strategic purpose: type 1, which installs functionality that is used to establish the carbon skeleton of the target; type 2, which is used to construct a heterocyclic ring; and type 3, which installs peripheral functional groups. The reactions are further divided based on whether they are directed or undirected. For each classification, examples from recent literature are analysed. Finally, we provide two case studies of syntheses from our laboratory that were streamlined by the judicious use of C–H oxidation reactions.

未活化的 C-H 键的氧化已成为天然产物合成中的一种有效策略，并改变了化学家合成复杂分子的方式。C-H氧化方法的使用通过扩大起始材料的选择、限制官能团相互转化和保护基团操作以及实现后期多样化，简化了合成计划的过程。在这篇综述中，我们根据 C-H 氧化的战略目的提出了分类： 类型 1，安装用于建立目标碳骨架的功能；类型2，用于构造杂环；类型 3，安装外围功能组。根据反应是定向的还是无向的，反应进一步划分。对于每个分类，都分析了最近文献中的例子。最后，我们提供了我们实验室的两个合成案例研究，这些合成案例通过明智地使用 C-H 氧化反应而得到简化。