1: 3-bromo-9-phenylcarbazole With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; hexane T=20°C; 8 h;

tris-(dibenzylideneacetone)dipalladium(0) in 1,4-dioxane

N-bromosuccinmide in dichloromethane; water; N,N-dimethyl-formamide

1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; hexane T=-78 - 20°C;

1: potassium carbonate; 18-crown-6 ether; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium(0) / toluene; xylene / 18 h / Inert atmosphere; Reflux 2: N-bromosuccinmide / N,N-dimethyl-formamide / 0 °C 3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere View Scheme

1: potassium carbonate; 18-crown-6 ether; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium(0) / toluene; xylene / 18 h / Inert atmosphere; Reflux 2: N-bromosuccinmide / N,N-dimethyl-formamide / 0 °C 3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere View Scheme

1.1: copper; potassium carbonate / N,N-dimethyl-formamide / 140 °C / Inert atmosphere 2.1: N-bromosuccinmide / N,N-dimethyl-formamide / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: -78 - 20 °C View Scheme

tris-(dibenzylideneacetone)dipalladium(0) in water; toluene

N2; tris-(dibenzylideneacetone)dipalladium(0); Pd2(dba)3 in tetrahydrofuran; anhydrous xylene; hexane; dichloromethane; toluene