dichloro bis(acetonitrile) palladium(II); tributyl-amine; tetra-n-butylammonium acetate; zinc oxide in dimethyl sulfoxide T=140°C; 30 h;

phosphorus pentoxide in dichloromethane 1 h; Ambient temperature;

1: imidazole / dimethylformamide / 1.5 h 2: 2) NaBH4 / 1) ether, 6 h, reflux, 2) MeOH, overnight 3: 95 percent / DMAP, Et3N / CH2Cl2 / Ambient temperature 4: 75 percent / P2O5 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 2) NaBH4 / 1) ether, 6 h, reflux, 2) MeOH, overnight 2: 95 percent / DMAP, Et3N / CH2Cl2 / Ambient temperature 3: 75 percent / P2O5 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 95 percent / DMAP, Et3N / CH2Cl2 / Ambient temperature 2: 75 percent / P2O5 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 50 °C / Inert atmosphere 2: hydroxylamine hydrochloride / acetonitrile / 10 - 12 h / 20 °C 3: zinc(II) chloride / 1,4-dioxane / 12 h / 110 °C 4: dichloro bis(acetonitrile) palladium(II); tributyl-amine; tetra-n-butylammonium acetate; zinc oxide / dimethyl sulfoxide / 30 h / 140 °C View Scheme

1: hydroxylamine hydrochloride / acetonitrile / 10 - 12 h / 20 °C 2: zinc(II) chloride / 1,4-dioxane / 12 h / 110 °C 3: dichloro bis(acetonitrile) palladium(II); tributyl-amine; tetra-n-butylammonium acetate; zinc oxide / dimethyl sulfoxide / 30 h / 140 °C View Scheme

1: zinc(II) chloride / 1,4-dioxane / 12 h / 110 °C 2: dichloro bis(acetonitrile) palladium(II); tributyl-amine; tetra-n-butylammonium acetate; zinc oxide / dimethyl sulfoxide / 30 h / 140 °C View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 50 °C / Inert atmosphere 2: hydroxylamine hydrochloride / acetonitrile / 10 - 12 h / 20 °C 3: zinc(II) chloride / 1,4-dioxane / 12 h / 110 °C 4: dichloro bis(acetonitrile) palladium(II); tributyl-amine; tetra-n-butylammonium acetate; zinc oxide / dimethyl sulfoxide / 30 h / 140 °C View Scheme