1: With n-butyllithium in tetrahydrofuran; hexane; toluene T=-50°C; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane; toluene T=-50 - -15°C; 3: With sodium hydroxide in tetrahydrofuran; hexane; toluene

hydrogenchloride; n-butyllithium in tetrahydrofuran anhydride; ethyl acetate

1: 2-methoxy-5-bromo-pyridine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - -20°C; 3: With hydrogenchloride; water in tetrahydrofuran; hexane pH=5;

1: sodium methylate / methanol / 0.5 h / |Reflux 2: n-butyllithium; boric acid trimethyl ester / tetrahydrofuran / -75.1 - 20 °C / |Inert atmosphere View Scheme

1: potassium carbonate; palladium diacetate; triphenylphosphine / water; ethylene glycol dimethyl ether / 5.67 h / |Reflux 2: hydrogenchloride / water / 3 h / |Reflux 3: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 4: N-bromosuccinmide / N,N-dimethyl-formamide / 2.5 h / 20 °C 5: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / |Inert atmosphere View Scheme

1: potassium carbonate; palladium diacetate; triphenylphosphine / water; ethylene glycol dimethyl ether / 5.67 h / |Reflux 2: hydrogenchloride / water / 3 h / |Reflux View Scheme

N,N-dimethyl-N-(4'-methylphenyl)amine N-oxide in dichloromethane T=20°C; 0.0166667 h;

sodium carbonate; bis-triphenylphosphine-palladium(II) chloride in 1,4-dioxane Suzuki-Miyaura cross-coupling reaction; 65 h; Heating;

copper(I) thiophene-2-carboxylate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane T=100°C; 12 h;

potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tri-cyclo-hexyl-phosphine in 1,4-dioxane; water T=100°C; 18 h;