potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in acetonitrile T=45°C; P=760 Torr;

copper(l) iodide; 1,10-phenanthroline; lithium carbonate in N,N-dimethyl-formamide T=100°C; 48 h; Sealed tube;

1: iodobenzene With palladium diacetate; caesium carbonate; di-(1-adamantyl)-n-butylphosphine in N,N-dimethyl-formamide T=100°C; 0.166667 h; Inert atmosphere; 2: C16H11NO in N,N-dimethyl-formamide T=100°C; 3 h; Inert atmosphere;

1.1: i-Pr2NH; CuI / Pd(PPh3)2Cl2 / dimethylformamide 1.2: 87 percent / dimethylformamide / 1.5 h / 0 - 20 °C 2.1: tetrahydrofuran / 1.5 h / 0 °C 3.1: 60 percent / K2CO3 / Pd(PPh3)4 / acetonitrile / 45 °C View Scheme

1: tetrahydrofuran / 1.5 h / 0 °C 2: 60 percent / K2CO3 / Pd(PPh3)4 / acetonitrile / 45 °C View Scheme

1.1: i-Pr2NH; CuI / Pd(PPh3)2Cl2 / dimethylformamide 1.2: 87 percent / dimethylformamide / 1.5 h / 0 - 20 °C 2.1: tetrahydrofuran / 1.5 h / 0 °C 3.1: 60 percent / K2CO3 / Pd(PPh3)4 / acetonitrile / 45 °C View Scheme

1.1: trichlorophosphate; triethylamine / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 2.1: palladium diacetate; di-(1-adamantyl)-n-butylphosphine; caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 100 °C / |Inert atmosphere 2.2: 3 h / 100 °C / |Inert atmosphere View Scheme

1.1: Pd2(PPh3)2Cl2; copper(l) iodide / triethylamine / 24 h / 20 °C / |Inert atmosphere 2.1: trichlorophosphate; triethylamine / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 3.1: palladium diacetate; di-(1-adamantyl)-n-butylphosphine; caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 100 °C / |Inert atmosphere 3.2: 3 h / 100 °C / |Inert atmosphere View Scheme

methyl-magnesium iodide 1.) Et2O, 1 h, 2.) 0 deg C; Yield given. Multistep reaction;