1: 76 percent / PdCl2(PhCN)2; AsPh3; CuI / 1-methyl-pyrrolidin-2-one / 20 h / 80 °C 2: 74 percent / CO; dppp; 1,10-phenanthroline monohydrate / Pd(dba)2 / dimethylformamide / 24 h / 80 °C / 4560 Torr View Scheme

copper(l) iodide; triphenyl-arsane; bis(benzonitrile)palladium(II) dichloride in 1-methyl-pyrrolidin-2-one T=80°C; Stille coupling; 48 h;

copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane in 1-methyl-pyrrolidin-2-one T=80°C; 48 h; Title compound not separated from byproducts;

1: 1-iodo-2-nitro-benzene With n-butyllithium in tetrahydrofuran; hexane 0.216667 h; Inert atmosphere; 2: tributyltin chloride in tetrahydrofuran; diethyl ether; hexane T=20°C; 1 h; Inert atmosphere;

tetrakis(triphenylphosphine) palladium(0) in toluene byproducts: (C4H9)3SnI; soln. of Bu3SnSnBu3, Pd(PPh3)4, aryl iodide in toluene heated to 80°C for 72 h under Ar; evapd., washed with aq. KF, extd. (C6H6), dried over Na2SO4, chromd. (SiO2, hexane); elem. anal.;

tetrakis(triphenylphosphine) palladium(0) in toluene byproducts: Bu3SnBr, o,o'-di-NO2-biphenyl; heating at 80°C with stirring under Ar atm., reaction completed when color of the soln. changed to black; solvent evapd., biaryl filtered off after recrystn., filtrate washed with aq. KF, organic layer extd. with benzene, dried over sodium sulfate, product chromd.;

1: 65 percent / PdCl2(PhCN)2; AsPh3; CuI / 1-methyl-pyrrolidin-2-one / 20 h / 80 °C 2: 86 percent / CO; dppp; 1,10-phenanthroline monohydrate / Pd(dba)2 / dimethylformamide / 72 h / 80 °C / 4560 Torr View Scheme

1: 75 percent / triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 2: 93 percent / hydrogen / palladium on carbon / methanol / 2 h / 20 °C / 760 Torr View Scheme