Cu-CATALYZED AZIDE-ALKYNE CYCLOADDITION: PREPARATION OF TRIS((1-BENZYL-1H-1,2,3- TRIAZOLYL)METHYL)AMINE

摘要

Caution! This procedure employs benzyl azide, which is an energetic and potentially explosive material. All transformations should be performed behind a blast shield in a well-ventilated fume hood. Tris((1-benzyl-1H-1,2,3-triazolyl)methyl)amine. A 100-mL two-necked, round-bottomed flask equipped with a football-shaped magnetic stir bar (25 x 15 mm), condenser and thermometer (Note 1) is charged with 45 mL of MeCN (Note 2). Copper(II) acetate, monohydrate (0.0610 g, 0.305 mmol, 0.02 equiv) (Note 3) is added as a powder and the reaction mixture is stirred vigorously at room temperature until a bright blue solution is obtained. Tripropargylamine (2.00 g, 15.2 mmol, 1.00 equiv) (Note 3) and benzyl azide (3.67 g, 25.9 mmol, 1.70 equiv) are dissolved in MeCN (10 mL) (Notes 2 and 4) and added to the reaction flask, which is then immersed into a water bath. Sodium ascorbate (0.061 g, 0.31 mmol, 0.02 equiv) (Note 3) is dissolved in water (5 mL) (Note 2), and the resulting solution is added in one portion to the reaction mixture (Note 5). The reaction mixture is stirred at room temperature for 30 min (Note 6) and then heated at 45 °C (internal temperature) for 5 h.