A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry.
A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry.
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DOI：
10.1039/d0sc04387g
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发表时间：
2020-10-20
期刊：
影响因子：
8.4
通讯作者：
Leonori D
中科院分区：
文献类型：
--
作者：
Constantin T;Juliá F;Sheikh NS;Leonori D
由于其高负还原电位，通过氧化还原化学从相应的卤化物生成芳基自由基通常被认为是一项艰巨的任务。在这里，我们证明α-氨基烷基自由基可以用作芳基卤化物与吡咯衍生物自由基偶联的引发剂和链载体，这种转化通常用于评估新型高还原性光催化剂。这种反应模式避免了使用强还原性物质，并且也能形成 sp2 C-P 键。机理研究已经描述了触发芳基自由基生成并传播链过程的一些关键特征。氨基烷基可用作将芳基卤转化为相应自由基的引发剂和链载体。这种方法绕过了强还原光催化剂的要求。
The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C–P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process. Aminoalkyl radicals can be used as both initiators and chain-carriers for the conversion of aryl halides into the corresponding radicals. This approach by-passes the requirement for strongly reducing photocatalysts.
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