Direct Assembly of Diverse Unsymmetrical Tertiary 9-Fluorenols via Transient Directing Group-Enabled Palladium-Catalyzed Dual C–H Bond Activation of α-Ketoesters,The Journal of Organic Chemistry

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Direct Assembly of Diverse Unsymmetrical Tertiary 9-Fluorenols via Transient Directing Group-Enabled Palladium-Catalyzed Dual C–H Bond Activation of α-Ketoesters
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.joc.2c01080
Wengang Xu ₁ , Yangyang Zhang ₁ , Yongdi Wu ₁ , Jian Wang ₁ , Xuelian Lu ₂ , Yirong Zhou ₃ , Fang-Lin Zhang _{1,

2}

Affiliation

An expeditious construction of an unsymmetrical tertiary 9-fluorenol skeleton was accomplished starting from readily available α-ketoester and aryl iodide. Inexpensive commercially available substituted aniline was utilized as a potent monodentate transient directing group (TDG) to assist palladium-catalyzed direct ortho-C–H arylation and tandem dual C–H activation of α-ketoesters to form two carbon–carbon bonds. To demonstrate practical applications, the reaction was enlarged to the gram scale, and subsequent one-step derivatization allowed facile access to structurally diversified useful derivatives. A series of control experiments were carried out to shed light on the possible catalytic mechanism.

中文翻译：

通过瞬时导向基团启用的钯催化双 C-H 键活化 α-酮酯直接组装不同的不对称叔 9-芴醇

从容易获得的α-酮酯和芳基碘化物开始，快速构建了不对称的叔 9-芴醇骨架。廉价的市售取代苯胺被用作有效的单齿瞬态导向基团 (TDG)，以帮助钯催化的直接邻 C-H 芳基化和串联双 C-H 活化 α-酮酯以形成两个碳-碳键。为了证明实际应用，将反应扩大到克级，随后的一步衍生化可以轻松获得结构多样化的有用衍生物。进行了一系列对照实验以阐明可能的催化机制。

更新日期：2022-08-03

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