1: 2-methylphenylmagnesium chloride With zinc(II) chloride in 1-methyl-pyrrolidin-2-one; diethyl ether T=60°C; 0.333333 h; 2: 1-Bromonaphthalene With ((Cy2POH)2PdCl)2 in 1-methyl-pyrrolidin-2-one T=65°C; Negishi cross-coupling; 2 h; Further stages.;

1: triallyl(2-methylphenyl)silane With tetrabutyl ammonium fluoride in water; dimethyl sulfoxide T=20°C; 1 h; 2: 1-Bromonaphthalene With tri-cyclo-hexyl-phosphine; palladium dichloride in water; dimethyl sulfoxide T=80°C; 20 h;

tris(dibenzylideneacetone)dipalladium (0); c-{P[-N(Bn)-CH2-CH2-]2N[-CH2-CH2-N(iBu)]}; cesium fluoride in 1,4-dioxane T=20°C; Stille cross-coupling; 48 h;

1: 1-Bromonaphthalene With magnesium in tetrahydrofuran 2: 1-bromo-2-methyl benzene With tris(dibenzylideneacetone)dipalladium (0) in tetrahydrofuran T=25°C; Kumada-Corriu cross-coupling; 15 h; Further stages.;

C16H16Cl2CoN8(1+)*F6P(1-) in tetrahydrofuran T=20°C; Kumada-Corriu cross-coupling; 2 h;

Multistep reaction;

1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; triethylamine; pyridine / 12 h / 80 °C / |Inert atmosphere; |Schlenk technique 2.1: potassium carbonate; water / tetrahydrofuran; methanol / 5 h / 20 °C / |Inert atmosphere; |Schlenk technique 3.1: triethylamine; [RhCl(η2:η2-cycloocta-1,5-diene)]2; tri-iso-propyl phosphine / cyclohexane / 0.5 h / 10 °C / |Inert atmosphere; |Schlenk technique 3.2: 12 h / 10 - 15 °C / |Inert atmosphere; |Schlenk technique 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide / tetrahydrofuran / 12 h / 50 °C / |Inert atmosphere; |Schlenk technique 5.1: potassium hydroxide; PEPPSITM-IPr / toluene; water / 12 h / 80 °C / |Inert atmosphere; |Schlenk technique 6.1: tri-cyclo-hexyl-phosphine; caesium carbonate; 2,2,2-trimethylacetic acid / 20 h / 20 - 150 °C / |Schlenk technique; |Inert atmosphere View Scheme

2: 55 percent / Zn, AcOH / 14 h / Heating View Scheme

2,2,6,6-tetramethylpiperidinyl-lithium in tetrahydrofuran

2,2,6,6-tetramethylpiperidinyl-lithium in various solvent(s) 0.5 h; Heating;