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note
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6 (0.010 mmol, 5 mol %) in dry chloroform (2 mL) was stirred at room temperature for 30 min. An aldehyde (0.20 mmol) and an aromatic amine (0.20 mmol) were added, and the whole mixture was stirred for an additional 15 min at the same temperature. The reaction mixture was cooled to 0 °C, and an alkyne (0.30 mmol) was added. The reaction mixture was allowed to warm to 20-25 °C. After completion of the reaction (monitoring by TLC), the mixture was concentrated in vacuo and purified over silica gel by column chromatography (2-10% EtOAc in hexane) yielding pure propargylamine.
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