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A general procedure for aromatic aldimines

XG Xu-Cheng Gan
CZ Cheng-Yuan Zhang
FZ Feng Zhong
PT Ping Tian
LY Liang Yin
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A dried 25-mL schlenk tube equipped with a magnetic stirring bar was charged with mesitylcopper (1.8 mg, 0.01 mmol, 5.0 mol %) and (R,Rp)-TANIAPHOS (6.8 mg, 0.01 mmol, 5.0 mol %) in a glove box under Ar atmosphere. Anhydrous DME (2 mL) was added via a syringe. The mixture was stirred for 20 min at room temperature to give a yellow solution. The reaction mixture was cooled to −30 °C, and benzyl imine (0. 2 mmol, 1.0 equiv) and N-Boc-aldimine (0.3 mmol, 1.5 equiv) were added. The resulting reaction mixture was stirred at −30 °C for 18 h. Then, the reaction mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 12/1) to give the desired product.

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