This thesis presents site-selective Suzuki-Miyaura reactions of 2,3,5-tribromo-thiophene, 2,4,5-tribromothiophene and 2,3,5-tribromo-N-methylpyrrole, which are controlled by steric and electronic parameters. Palladium-catalyzed Heck reactions of brominated thiophenes, N-methylimidazole, N-methylpyrrole and N-methylindole are also presented. The products were transformed by subsequent 6p-electrocyclization and dehydrogenation to functionalized benzothiophenes, dibenzothiophenes, benzimidazoles, indoles and carbazoles, respectively.
