Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO,Chemical Science

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Intermolecular radical oxyalkylation of arynes with alkenes and TEMPO
Chemical Science ( IF 7.6 ) Pub Date : 2024-07-26 , DOI: 10.1039/d4sc04369c
Debkanta Bhattacharya ₁ , Maximilian Scherübl ₁ , Constantin G Daniliuc ₁ , Armido Studer ₁

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Radical transformations with arynes represent an underexplored research field and only a few examples have been disclosed. In this research article, the implementation of arynes in three-component reactions with TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) and activated alkenes is demonstrated. TEMPO is added to arynes, which triggers a Meerwein-type arylation cascade where the final alkyl radial is eventually trapped by a second equivalent of TEMPO. This method is applicable to activated alkenes such as electron-deficient acrylates, styrenes and also vinyl acetate to provide various bisalkoxyamines. This work is a contribution to the emerging field of radical aryne chemistry.

中文翻译：

芳烃与烯烃和 TEMPO 的分子间自由基烷氧基化

芳炔的激进转化代表了一个尚未充分探索的研究领域，并且仅公开了几个例子。在这篇研究文章中，演示了芳炔在与 TEMPO（2,2,6,6-四甲基哌啶 1-氧基）和活化烯烃的三组分反应中的实施。 TEMPO 添加到芳烃中，引发 Meerwein 型芳基化级联，其中最终的烷基自由基最终被第二个当量的 TEMPO 捕获。该方法适用于活化烯烃，例如缺电子丙烯酸酯、苯乙烯以及乙酸乙烯酯，以提供各种双烷氧基胺。这项工作是对自由基芳炔化学这一新兴领域的贡献。

更新日期：2024-07-26

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