The research presented in this work comprehensively describes hydrosilylation of a wide spectrum of alkenes which contain one or more reactive groups with (HSiMe O)(iBu) Si O , in the presence of different types of catalysts. Special attention is paid to the influence of alkene, catalyst, and reaction conditions on process effectiveness and selectivity by the precise monitoring of the experiments with in situ FTIR and NMR spectroscopies. More than twenty silsesquioxanes bearing reactive groups (OH, Br, NR , CO, COOR, NCO, epoxy, SiR ) commonly used in organic and polymer chemistry, were obtained, isolated and characterized by H, C, Si NMR and MALDI TOF. Importantly, in the presented syntheses, commercially available reagents and catalysts were used, meaning that the presented methods could be easily repeated, rapidly scaled up, and widely applied.