In this project, amines, boronic acids, and carbonyl compounds will be used as building blocks in solid-state reactions. The focus will be on reactions of boron reagents that are often used in solution-phase chemistry but whose solid-state reactivity has so far not been investigated. In addition to classical ball-milling reactions, photomechanochemical reactions in the presence of boronic acid derivatives will be explored. The use of in situ Raman spectroscopy and ex situ diffraction and spectroscopic methods will enable characterization of the species involved in the reactions, providing insight into the reaction pathway and the factors that control reactivity and selectivity. The preparation of selected products with potential biological or pharmaceutical applications will also be tested on a larger scale using an twin-screw extruder. The same reactions will be tested and spectroscopically monitored in solution. Quantum-chemical calculations will be used to rationalize the experimental data. The mechanochemical methods developed will provide an environmentally friendly approach to the compounds under investigation. Moreover, understanding the reaction dynamics will significantly aid future design of solid-state reactions involving boron reagents.