hydrogen; palladium in ethyl acetate T=20°C; 4 h;

2,6-di-tert-butyl-4-methyl-phenol; bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=40 - 55°C; Stille reaction; 68 h;

1: 84 percent / K2CO3 / acetone / 25 °C 2: 70 percent / 2,6-di-t-butyl-4-methylphenol / (Ph3P)2Pd(II)Cl2 / dimethylformamide / 68 h / 40 - 55 °C View Scheme

1: N-ethyl-N,N-diisopropylamine; 5 Pd/C; triphenylphosphine; copper(l) iodide / 8 h / 80 °C / |Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 3: hydrogen; palladium / ethyl acetate / 4 h / 20 °C View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 20 °C 2: hydrogen; palladium / ethyl acetate / 4 h / 20 °C View Scheme

ammonium chloride; acetic acid in water 4 h; Reflux;

ammonium chloride in water; acetic acid 5 h; Heating;