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Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids.
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2020-03-25 , DOI: 10.1002/chem.202000902
Alexander Mamontov 1, 2 , Agnès Martin-Mingot 1 , Benoit Métayer 1, 2 , Omar Karam 2 , Fabien Zunino 2 , Fodil Bouazza 2 , Sébastien Thibaudeau 1
Affiliation  

Site‐selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long‐standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2−H bonds of aromatic amines occurs. Furthermore, the superacid‐promoted (poly)protonation of the molecules acts as a protection, favoring the late‐stage selective halogenation of natural alkaloids and active pharmaceutical ingredients

中文翻译:

含氮(杂)芳烃与超强酸的互补位点选择性卤化。

与经典的芳香族取代反应互补的芳烃的位点选择性官能化仍然是有机合成中的长期追求。通过利用氧化过程中的ion离子的产生和HF / SbF 5中含氮功能的质子化,芳香胺的经典惰性Csp 2 -H键发生氯化和碘化。此外,分子的超强酸促进(聚)质子化作用起到保护作用,有利于天然生物碱和活性药物成分的后期选择性卤化
更新日期:2020-03-25
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