toluene-4-sulfonic acid in benzene 72 h; Heating;

[2,2']bipyridinyl; nickel diacetate; sodium tert-pentoxide in tetrahydrofuran T=25°C; 0.00472222 h;

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 76 percent / p-toluenesulfonic acid / acetone / 18 h / Heating View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 76 percent / p-toluenesulfonic acid / acetone / 18 h / Heating 3: 35 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 4: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 5: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 94 percent / aq. 80percent acetic acid / 0.5 h / 70 °C 3: 1. p-toluenesulfonyl chloride; 2. 20percent aq. NaOH / 1. pyridine, r.t., 1d; 2. 1.5N sulfuric acid, ice-bath; 3. DMSO, r.t., 1h 4: 33 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 5: 71 percent / p-toluenesulfonyl chloride, NaOH / acetone; H2O / 3 h View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 94 percent / aq. 80percent acetic acid / 0.5 h / 70 °C View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 94 percent / aq. 80percent acetic acid / 0.5 h / 70 °C 3: 1. p-toluenesulfonyl chloride; 2. 20percent aq. NaOH / 1. pyridine, r.t., 1d; 2. 1.5N sulfuric acid, ice-bath; 3. DMSO, r.t., 1h View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 94 percent / aq. 80percent acetic acid / 0.5 h / 70 °C 3: 1. p-toluenesulfonyl chloride; 2. 20percent aq. NaOH / 1. pyridine, r.t., 1d; 2. 1.5N sulfuric acid, ice-bath; 3. DMSO, r.t., 1h 4: 36 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating View Scheme