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Mechanochemical halogenation of unsymmetrically substituted azobenzenes

Barišić, Dajana; Pajić, Mario; Halasz, Ivan; Babić, Darko; Ćurić, Manda (2022) Mechanochemical halogenation of unsymmetrically substituted azobenzenes. Beilstein journal of organic chemistry, 18 . pp. 680-687. ISSN 2195-951X

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The direct and selective mechanochemical halogenation of C–H bonds in unsymmetrically substituted azobenzenes using N-halosuccinimides as the halogen source under neat grinding or liquid-assisted grinding conditions in a ball mill has been described. Depending on the azobenzene substrate used, halogenation of the C–H bonds occurs in the absence or only in the presence of PdII catalysts. Insight into the reaction dynamics and characterization of the products was achieved by in situ Raman and ex situ NMR spectroscopy and PXRD analysis. A strong influence of the different 4, 4’-substituents of azobenzene on the halogenation time and mechanism was found.

Item Type: Article
Uncontrolled Keywords: azo compounds ; halogenation ; mechanochemistry ; N-halosuccinimide ; palladium(II)
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Mehanokemijska aktivacija i funkcionalizacija veze C–H potaknuta paladijem i usmjerena ligandomĆurić, MandaIP-2019-04-9951HRZZ
Sistematika mehanizama u bezotopinskoj ili tekućinski kataliziranoj sintezi u čvrstom stanju-SystForSyntIvan HalaszIP-2020-02-1419HRZZ
Depositing User: Dajana Barišić
Date Deposited: 29 Jun 2022 13:09
DOI: 10.3762/bjoc.18.69

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