Mechanochemical methods are being developed for the selective halogenation of C–H bonds in aromatic substrates related to the preparation of substrates by the Suzuki-Miyaura (SM) reaction and the synthesis of B←N adducts of phenylboronic acid with a series of amines of different structure and basicity. The effects of different catalysts, bases, additives and substrates on the course and utilization of SM reactions in the solid state and new organopalladium catalysts for the SM cross-coupling of azobenzene derivatives and boronic acids will be investigated. The dynamics of product formation in mechanochemical reactions will be monitored and analyzed by in situ Raman spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy and ex situ X-ray diffraction on a powder sample (PXRD).