hydrogenchloride; hydrogen; palladium on carbon catalyst in ethyl acetate P=2250.23 Torr;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in dimethyl sulfoxide T=120°C;

acetic acid in ethanol

1-methyl-1H-imidazole; [2,2']bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile T=60°C; 24 h; Molecular sieve;

1: palladium 10 on activated carbon / methanol / 65 h 2: 1-methyl-1H-imidazole; [2,2']bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 60 °C / Molecular sieve View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 4.5 h / 20 °C / Inert atmosphere 2: palladium 10 on activated carbon / methanol / 65 h 3: 1-methyl-1H-imidazole; [2,2']bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 60 °C / Molecular sieve View Scheme