Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids

Autor: Omar Karam, Fabien Zunino, Agnès Martin-Mingot, Sébastien Thibaudeau, Alexander Mamontov, Benoît Métayer, Fodil Bouazza
Rok vydání: 2020
Předmět:
Zdroj: Chemistry – A European Journal. 26:10411-10416
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.202000902
Popis: 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.
Databáze: OpenAIRE
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