potassium carbonate in acetone 20 h; Heating;

potassium carbonate in acetonitrile Heating;

1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 70 °C View Scheme

toluene

1: 1.) Mg, 2.) CuBr*Me2S, Me2S / 1) THF, reflux, 15 min; 2) THF, -50 deg C, 3 min; 3) THF, 10 deg C, 2 h 2: 90 percent / LiOH, H2O2 / tetrahydrofuran; H2O 3: 1.) SOCl2 / 1) benzene, 50 deg C, 50 min; 2) ether, rt, 1.5 h 4: 1.) LiAlH4, 2.) H2 / 2.) Pd/C / 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight View Scheme

copper(l) iodide; triphenylphosphine; palladium dichloride in triethylamine; N,N-dimethyl-formamide

1.1: tert-butyllithium / tetrahydrofuran; pentane / 1.17 h / -78 °C 1.2: zinc chloride / tetrahydrofuran; pentane; diethyl ether / -78 - 20 °C 1.3: Pd(PPh3)4 / tetrahydrofuran; pentane; diethyl ether / 24 h / Heating 2.1: 0.920 g / lithium; ammonia / diethyl ether / 1.5 h / cooling View Scheme

2,2'-azo-bisisobutyronitrile; 1,1,2,2-tetraphenyldisilane in m-xylene 22 h; Heating;

1: 1-((2-bromo-4-methylphenoxy)methyl)benzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78 - 20°C; 12 h; Further stages.;