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Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids
Author(s) -
Mamontov Alexander,
MartinMingot Agnès,
Métayer Benoit,
Karam Omar,
Zunino Fabien,
Bouazza Fodil,
Thibaudeau Sébastien
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000902
Subject(s) - halogenation , protonation , superacid , chemistry , electrophilic aromatic substitution , inert , nitrogen , surface modification , organic chemistry , combinatorial chemistry , catalysis , ion
Abstract 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/SbF 5 , the chlorination and iodination of classically inert Csp 2 −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