Mechanochemical halogenation of unsymmetrically substituted azobenzenes

被引：10

作者：

Barisic, Dajana ^{[1
]}

Pajic, Mario ^{[1
]}

Halasz, Ivan ^{[1
]}

Babic, Darko ^{[1
]}

Curic, Manda ^{[1
]}

机构：

[1] Rudjer Boskovic Inst, Div Phys Chem, Bijenicka Cesta 54, Zagreb, Croatia

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 18卷

关键词：

azo compounds; halogenation; mechanochemistry; N-halosuccinimide; palladium(II); H BOND ACTIVATION; SOLVENTLESS CONDITIONS; (HETERO)ARYL HALIDES; FUNCTIONALIZATIONS; ACETANILIDES; REAGENTS; ALKYNES; COBALT;

D O I：

10.3762/bjoc.18.69

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：680 / 687

页数：8

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