1: 3,6-dibromo-9-octyl-9H-carbazole With sec.-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.333333 h; Inert atmosphere; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; hexane T=-78°C; 24 h; Inert atmosphere;

bis-triphenylphosphine-palladium(II) chloride; potassium acetate in toluene T=110°C; Miyaura Borylation Reaction; 18 h; Inert atmosphere;

1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water; benzene / 12 h / 90 °C 2.1: N-bromosuccinmide / chloroform / 8 h / 40 °C 3.1: sec.-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere 3.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

1.1: N-bromosuccinmide / chloroform / 8 h / 40 °C 2.1: sec.-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere 2.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water; benzene / 12 h / 90 °C 2.1: N-bromosuccinmide / chloroform / 8 h / 40 °C 3.1: sec.-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere 3.2: 24 h / -78 - 20 °C / Inert atmosphere View Scheme

1: tetrabutylammomium bromide; potassium hydroxide / acetone / 6 h / |Reflux 2: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / toluene / 18 h / 110 °C / |Inert atmosphere View Scheme