TY - JOUR A1 - Barišić, Dajana A1 - Pajić, Mario A1 - Halasz, Ivan A1 - Babić, Darko A1 - Ćurić, Manda T1 - Mechanochemical halogenation of unsymmetrically substituted azobenzenes JF - Beilstein Journal of Organic Chemistry PY - 2022/// VL - 18 SP - 680 EP - 687 SN - 1860-5397 DO - 10.3762/bjoc.18.69 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.18.69 KW - azo compounds KW - halogenation KW - mechanochemistry KW - N-halosuccinimide KW - palladium(II) N2 - 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. ER -