Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ

Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
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DOI:
10.1002/anie.201309761
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发表时间:
2014-02-17
影响因子:
16.6
通讯作者:
Carrillo, Romen
Carrillo, Romen
中科院分区:
化学1区
文献类型:
--
作者:
Pinacho Crisostomo, Fernando;Martin, Tomas;Carrillo, Romen

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抗坏血酸(维生素C)已用作(杂)芳烃无金属直接CH芳基化反应中的自由基引发剂。从苯胺开始,原位生成相应的芳烃重氮离子,并立即被维生素C还原为芳基,该芳基用(杂)芳烃进行均裂芳族取代。值得注意的是,既不需要加热也不需要照射。该方法温和,操作简单,是一种更环保的芳基化方法。
Ascorbic acid (vitaminC) has been used as a radical initiator in a metal-free direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitaminC to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.