1: 37 percent / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 60 °C 2: 1.) t-amyl alcohol, sodium hydride / 1.) THF, 25 deg C, 2.) benzene, DMSO, 60 deg C, 30 min View Scheme

1: 37 percent / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 60 °C 2: 77 percent / triphenylphosphine / 1.) dichloromethane, 5 deg C, 1 h, 2.) 20 deg C, overnight 3: 68 percent / potassium t-amylate / hexane / 1.) 0 - 20 deg C, 30 min, 2.) 20 deg C, overnight 4: 1.) butyl-lithium / 1.) THF, -78 deg C, 2 h, 2.) 48 h 5: 52.5 percent / pyridine / 48 h / 0 °C 6: 1.) potassium hydride, 2.) 18-crown-6 / 1.) THF, 0 deg C, 5 min, 2.) 1,2-dimethoxyethane, 80 deg C, overnight View Scheme

n-butyllithium; ethylmagnesium bromide; zinc(II) chloride; bis-triphenylphosphine-palladium(II) chloride 2) DMF, 25 deg C, overnight; Yield given. Multistep reaction;

triphenylphosphine in tetrahydrofuran T=70°C; Negishi Coupling; 24 h; Inert atmosphereGreen chemistry; Catalytic behavior;

palladium diacetate; triphenyl-arsane in tetrahydrofuran T=20°C; 23 h;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; benzene T=25°C;

triphenylphosphine in toluene T=110°C; Negishi Coupling; 24 h; Inert atmosphereGreen chemistry; Catalytic behavior;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=60°C;