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

Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids.
Chemistry. 2020 Mar 25;:
Authors: Mamontov A, Martin-Mingot A, Métayer B, Karam O, Zunino F, Bouazza F, Thibaudeau S
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 C sp2 -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.
PMID: 32212405 [PubMed - as supplied by publisher]

Source: Chemistry - March 24, 2020 Category: Chemistry Authors: Mamontov A, Martin-Mingot A, Métayer B, Karam O, Zunino F, Bouazza F, Thibaudeau S Tags: Chemistry Source Type: research