oxygen; sodium acetate; palladium diacetate; Hexadecyltrimethylammonium hydrogen sulfate in water T=23°C; 10 h;

1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium(0) T=80°C; 3 h;

1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium(0) T=80°C; 3 h;

styrene; [2,2']bipyridinyl; sodium hydride; bis(acetylacetonate)nickel(II); tris(2,4-pentanedionato-O,O')aluminum in tetrahydrofuran Ullmann coupling; 3 h; Heating;

1: p-toluidine With n-butyllithium; ZnCl2*TMEDA in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphereSchlenk technique; 2: (3,4-methylenedioxy)phenyl magnesium bromide With N,N'-dimethyl-N,N'-propyleneurea; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane in tetrahydrofuran; hexane T=0 - 20°C; 3 h; Inert atmosphereSchlenk technique;

anhydrous iron chloride; magnesium in tetrahydrofuran; ethylene dibromide Barbier reaction; 1 h; Reflux;

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 View Scheme

pyridine; 2,6-di-tert-butyl-4-methyl-phenol; hexamethyl-distannane; pyridine hydrogenfluoride; lithium chloride; tetrakis(triphenylphosphine) palladium(0) 1.) 1,4-dioxane, reflux, 22 h, 2.) THF, 23 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 4-methoxybenzenediazonium tetrafluoroborate With palladium diacetate in methanol Suzuki-Miyaura reaction; 0.166667 h; Inert atmosphere; 2: potassium 3,4-(methylenedioxy)phenyltrifluoroborate in methanol T=20°C; Suzuki-Miyaura reaction; 12 h; Inert atmosphere;

palladium diacetate; tri-tert-butyl phosphine in xylene T=120°C; Substitution; Suzuki coupling; 6 h;