Bhattacharya Debkanta, Scherübl Maximilian, Daniliuc Constantin G, Studer Armido
Organisch-Chemisches Institut, Universität Münster Corrensstraße 40 48149 Münster Germany
Chem Sci. 2024 Jul 26;15(34):13712-13716. doi: 10.1039/d4sc04369c. eCollection 2024 Aug 28.
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.
芳炔参与的自由基转化是一个尚未充分探索的研究领域，目前仅报道了少数例子。在这篇研究论文中，展示了芳炔在与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应用。将TEMPO加入到芳炔中，引发了一个类似Meerwein型的芳基化级联反应，最终生成的烷基自由基被第二个当量的TEMPO捕获。该方法适用于缺电子丙烯酸酯、苯乙烯以及醋酸乙烯酯等活化烯烃，可用于制备各种双烷氧基胺。这项工作为新兴的自由基芳炔化学领域做出了贡献。
