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16 [bmim]AuCl4 was prepared as follows: To a magnetically stirred solution of [bmim]Cl (0.0458 g, 0.263 mmol) in CH2Cl2 (5 mL) was added NaAuCl4·H2O (0.100 g, 0.263 mmol) and the reaction was allowed to stand at r.t. for 4 h. Then, the mixture was extracted with CH2Cl2 (100 mL) and H2O (2 × 50 mL). The organic layer was dried (Na2SO4) and evaporated to give [bmim]AuCl4 as a yellow powder (0.120 g).
17
Representative Procedure: To 2-(dec-1-ynyl)aniline (1f; 0.059 g, 0.26 mmol) in [bmim]BF4 (1 mL) was added NaAuCl4·2H2O (0.001 g, 1 mol%). The mixture was stirred at 50 °C for 24 h. The mixture was diluted with Et2O (100 mL) and washed with brine. The Et2O layer was dried (Na2SO4) and concentrated in vacuo and the residue was purified by flash chromatography on silica gel giving 2f (54 mg, 92% yield); mp 50-51 °C. IR (KBr): 3413, 2923, 1457, 1408, 774 cm-1. 1H NMR (CDCl3): δ = 7.86 (br s, 1 H), 7.57 (d, J = 7.6 Hz, 1 H), 7.32 (d, J = 7.7 Hz, 1 H), 7.25 (dt, J
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2 = 1.3 Hz, 1 H), 7.11 (dt, J
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Recycling Procedure: To a solution of 1a (0.100 g, 0.52 mmol) in [bmim]BF4 (2 mL) was added n-Bu4NAuCl4 (0.003 g, 1 mol%). The mixture was stirred at 50 °C for 24 h. The product was extracted from the reaction mixture by addition of Et2O (5 × 10 mL). The Et2O layer was separated. The ionic liquid layer containing the gold catalyst was pumped for several minutes and reused.
24
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