1,1'-bis-(diphenylphosphino)ferrocene; (9-phenanthrenyl)Ni(II)(PPh3)2Cl; potassium carbonate in toluene T=110°C; Suzuki Coupling; 18 h; Inert atmosphere;

potassium carbonate; Pd(Ph3P)4 in 1,4-dioxane; water

methyl(diphenyl)-phosphine; lithium chloride; palladium diacetate in N,N-dimethyl-formamide T=130°C; 26 h;

potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane; water 4 h; Heating / reflux;

caesium carbonate; tri-cyclo-hexyl-phosphine; palladium diacetate in tetrahydrofuran Suzuki-Miyaura reaction; 24 h; Heating;

dirhodium tetraacetate; 1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride; sodium t-butanolate in toluene T=95°C; 24 h; regioselective reaction;

1: 8-Chloroquinoline With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; di-(1-adamantyl)-n-butylphosphine in N,N-dimethyl acetamide T=90°C; 1 h; Inert atmosphere; 2: bromobenzene With potassium carbonate in water; N,N-dimethyl-aniline Suzuki coupling; Inert atmosphere;

lithium bromide in tetrahydrofuran T=20°C; 12 h;

1: 80 percent / pyridine / 1.) 0 deg C, 5 min, 2.) 23 deg C, 25 h 2: 1.) LiCl2,6-di-tert-butyl-4-methylphenol, 2.) 10percent aq. NH4OH / 1.) Pd(PPH3)4 / 1.) 1,4-dioxane, reflux, 82 h View Scheme

sulfuric acid; m-nitrobenzene sulfonic acid sodium salt