1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.08 h / -15 - -10 °C / Inert atmosphere 1.2: 0.5 h / -15 - 5 °C / Inert atmosphere 1.3: 2 h / 20 °C / Inert atmosphere 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: methanol; potassium carbonate / tetrahydrofuran / 20 °C / Inert atmosphere 4.1: 1,2-dichloro-benzene / 200 °C View Scheme

BTEAICl2 in methanol; dichloromethane Inert atmosphere;

1: With tert.-butyl lithium in tetrahydrofuran; pentane T=-20°C; 2 h; 2: in tetrahydrofuran; pentane T=-78 - 20°C; 3 h; regioselective reactionFurther stages;

1.1: tris-(dibenzylideneacetone)dipalladium(0); PtBu3; lithium hexamethyldisilazane / Inert atmosphere 1.2: Inert atmosphere 2.1: BTEAICl2 / methanol; dichloromethane / Inert atmosphere View Scheme

1.1: diphenyl phosphoryl azide; triethylamine / toluene / 24 h / Molecular sieve; Reflux 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -20 °C 2.2: diiodoethane / 3 h / -78 - 20 °C View Scheme

hydrogenchloride

1: acetic acid; iodine monochloride 2: aq.-ethanolic hydrochloric acid View Scheme

in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=100 - 110°C; 3 h;

1: 3,4-dihydronaphthalene-1(2H)-one With potassium tert-butylate in dimethyl sulfoxide 0.25 h; 2: 2-Amino-1-iodonaphthalene in dimethyl sulfoxide 3 h; Photolysis;