copper(l) iodide; Pd(AsPh3)2 in various solvent(s) T=100°C;

1: 77 percent / n-butyllithium / tetrahydrofuran; cyclohexane / 1.) 0 deg C, 20 min, 2.) 0 deg C, 30 min 2: 53 percent / (Me3Si)2NK / tetrahydrofuran; toluene / 1.) -78 deg C, 2. ) -78 deg C to room temp., overnight 3: 77 percent / Ph3As, bis(benzonitrile)palladium(II) chloride, CuI / various solvent(s) / 18 h / 100 °C View Scheme

1: 53 percent / (Me3Si)2NK / tetrahydrofuran; toluene / 1.) -78 deg C, 2. ) -78 deg C to room temp., overnight 2: 77 percent / Ph3As, bis(benzonitrile)palladium(II) chloride, CuI / various solvent(s) / 18 h / 100 °C View Scheme

1: 77 percent / n-butyllithium / tetrahydrofuran; cyclohexane / 1.) 0 deg C, 20 min, 2.) 0 deg C, 30 min 2: 53 percent / (Me3Si)2NK / tetrahydrofuran; toluene / 1.) -78 deg C, 2. ) -78 deg C to room temp., overnight 3: 77 percent / Ph3As, bis(benzonitrile)palladium(II) chloride, CuI / various solvent(s) / 18 h / 100 °C View Scheme

1: 1) nBuLi / 1) THF, 0 deg C, 2) THF, 0 to 20 deg C 2: 1) (Me3Si)2NK / 1) THF, -78 deg C, 2) THF, -78 to 20 deg C 3: 77 percent / Pd(AsPh3)2, CuI / various solvent(s) / 100 °C View Scheme

(i) NaH, THF, (ii) /BRN= 5790610/; Multistep reaction;