1: 3,4-(OCH2O)-C6H3-X, X = lithium or magnesium halide With titanium tetraethoxide in tetrahydrofuran T=0°C; 2: 2-chloro-quinoline With 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride; bis(acetylacetonate)nickel(II) in tetrahydrofuran T=25°C; 18 h; Further stages.;

oxygen; [IrHCl2(cod)]2 in dimethyl sulfoxide T=90°C; P=760.051 Torr; 12 h;

oxygen; [IrHCl2(cod)]2 in dimethyl sulfoxide T=90°C; P=760.051 Torr; 12 h;

iron tribromide in tetrahydrofuran; tert-butyl methyl ether T=20°C; 0.0833333 h; Inert atmosphereSchlenk technique;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; benzene 48 h; Heating;

1: quinoline With (2,2,6,6-tetramethylpiperidinyl)MgCl*LiCl; boron trifluoride diethyl etherate in tetrahydrofuran T=-40°C; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran T=-40°C; 0.5 h; Inert atmosphere; 3: 4-iodo-1,2-methylenedioxybenzene With P(o-furyl)3; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran T=-40 - 25°C; Negishi coupling reaction; Inert atmosphere; regioselective reaction;

palladium diacetate; potassium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in tetrahydrofuran T=80°C; Suzuki Coupling; 14 h; Inert atmosphere;

1: 79 percent / zinc / NiBr2(dppe) / acetonitrile / 12 h / 80 °C 2: TBAF / tetrahydrofuran / 1 h / 60 °C View Scheme

1: 87 percent / pyridine / 1.) 0 deg C, 5 min, 2.) 23 deg C, 25 h 2: 1.) LiCl, 2,6-di-tert-butyl-4-methylphenol, (Me3Sn)2 2.) pyridin, pyridinium hydrofluoride / 1.) Pd(PPH3)4 / 1.) 1,4-dioxane, reflux, 22 h, 2.) THF, 23 deg C, 16 h 3: 1.) LiCl, 2,6-di-tert-butyl-4-methylphenol, 2.) pyridin, pyridinium hydrofluoride / 1.) Pd(PPh3)4 / 1.) 1,4-dioxane, reflux, 68 h, 2.) THF, 23 deg C, 16 h View Scheme

1: 84 percent / pyridine / 1.) 0 deg C, 5 min, 2.) 23 deg C, 25 h 2: 1.) LiCl, 2,6-di-tert-butyl-4-methylphenol, 2.) pyridin, pyridinium hydrofluoride / 1.) Pd(PPh3)4 / 1.) 1,4-dioxane, reflux, 68 h, 2.) THF, 23 deg C, 16 h View Scheme