bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine 16 h; Ambient temperature;

1: NaOH / ethanol; tetrahydrofuran / 0.5 h 2: 77 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature 3: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 4: 94 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature View Scheme

1: 90 percent / PdCl2(PPh3)2, CuI, Et3N / 18 h / Ambient temperature 2: NaOH / ethanol; tetrahydrofuran / 0.5 h 3: 77 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature 4: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 5: 94 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature View Scheme

1: 77 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature 2: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 3: 94 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature View Scheme

1: 77 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature 2: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 3: 94 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature View Scheme

1: 90 percent / PdCl2(PPh3)2, CuI, Et3N / 18 h / Ambient temperature 2: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 3: 77 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature 4: 1.) NaNO2, conc. aq. HCl, 2.) KI / 1.) 0 deg C, 45 min, 2.) water, RT, overnight 5: 94 percent / PdCl2(PPh3)2, CuI, Et3N / 16 h / Ambient temperature View Scheme