1: 4-(N,N-diphenylamino)-bromobenzene With n-butyllithium in diethyl ether; hexane T=-50 - 25°C; 2: With copper(l) iodide in diethyl ether; hexane T=20°C; 3: allyl bromide in diethyl ether; hexane T=20°C; 12 h;

1: [4-(diphenylamino)phenyl][2-(hydroxymethyl)phenyl]dimethylsilane With n-butyllithium in tetrahydrofuran; hexane T=0°C; 0.5 h; Inert atmosphere; 2: 3-chloroprop-1-ene With copper(l) iodide; triethyl phosphite in N,N-dimethyl-formamide T=50°C; 16 h; Inert atmosphere;

1.1: tris(dibenzylideneacetone)dipalladium; bis(diphenylphosphino)ferrocene; t-BuONa / toluene / 0.25 h / 25 °C 1.2: 59 percent / toluene / 15 h / 90 °C 2.1: n-BuLi / diethyl ether; hexane / -50 - 25 °C 2.2: CuI / diethyl ether; hexane / 20 °C 2.3: 35 percent / diethyl ether; hexane / 12 h / 20 °C View Scheme

1.1: tris(dibenzylideneacetone)dipalladium; bis(diphenylphosphino)ferrocene; t-BuONa / toluene / 0.25 h / 25 °C 1.2: 59 percent / toluene / 15 h / 90 °C 2.1: n-BuLi / diethyl ether; hexane / -50 - 25 °C 2.2: CuI / diethyl ether; hexane / 20 °C 2.3: 35 percent / diethyl ether; hexane / 12 h / 20 °C View Scheme