C–H functionalization is among the hottest topics within modern chemistry. Indeed, otherwise unreactive C–H bonds can be considered today as regular functional groups for further chemical manipulation and such a concept has undoubtedly revolutionized the perception of organic chemistry when designing chemical syntheses. The aim of our research group relies on the development of innovative and sustainable procedures for the assembly of medicinally relevant compounds upon metal-catalyzed C–H functionalization reactions. In particular, we have followed two different strategies in this field: