Preparation and Reactions of Indoleninyl Halides: Scaffolds for the Synthesis of Spirocyclic Indole Derivatives

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• 作者：John T. R. Liddon ; Aimee K. Clarke ; Richard J. K. Taylor ; William P. Unsworth
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 16, 2016
• 年：2016
• 卷：18
• 期：24
• 页码：6328-6331
• 全文大小：458K
• ISSN：1523-7052

文摘

The dearomatization of 2-haloindole precursors allows access to indoleninyl halides, a hitherto underexploited functional handle with broad synthetic utility. Indoleninyl iodides have been shown to react via three distinct modes: hydrolysis, nucleophilic substitution, and cross-coupling. This allows a broad array of functionalized spirocyclic indole derivatives to be generated from a common starting material. They are also useful precursors to functionalized quinolines following migratory rearrangement and subsequent derivatization reactions.