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 |
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Rok vydání: | 2020 |
Předmět: |
Reaction mechanism
010405 organic chemistry Chemistry Organic Chemistry Halogenation chemistry.chemical_element Protonation General Chemistry Electrophilic aromatic substitution 010402 general chemistry 01 natural sciences Nitrogen Catalysis 0104 chemical sciences chemistry.chemical_compound Molecule Organic chemistry Surface modification Organic synthesis |
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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