Chapter one is split into three sections, providing general overviews of synthetic retinoids and their biology, Pd-catalysed C-C bond forming reactions and transition metal-catalysed borylation of aromatic and vinylic C-H bonds, respectively. Chapter two details the application of sequential Ir-catalysed aromatic C-H borylations, Pd-catalysed C-C bond forming reactions and Rh-catalysed vinylic C-H borylations for the stereo-controlled synthesis of stilbene-based TTNPB retinoids. Chapter three details the application of Ir-catalysed aromatic C-H borylations, Sonogashira cross-couplings and Suzuki-Miyaura cross-couplings for the synthesis of tolan-, and biaryl-based retinoids. Chapter four details the development and applications of new RhI catalyst precursors for the dehydrogenative borylation of unactivated olefins. The dehydrogenative borylation reactions were utilised in one-pot, single solvent syntheses of 2-arylindenes from indene and arylhalides through C-H borylation and subsequent Suzuki-Miyaura cross-couplings.