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2015年，勃林格殷格翰制药公司的Jonathan Reeves等人发现了一种新的制备亚胺的试剂B(OCH2CF3)3。它可以在温和条件下缩合酰胺或胺与羰基化合物制备各种亚胺，如 N-亚磺酰基, N-甲苯磺酰基, N-(二甲胺)磺酰基, N-二苯基次膦酰基, N-(α-甲基苄基) 和N-(4-甲氧基苯基) 醛亚胺。反应操作简单，无需特殊后处理，易于分离。 【Org. Lett. 2015, 17, 2442–2445】
一、制备Ellman亚胺
General Procedure for N-Sulfinyl Aldimine Formation. To a dry round bottom flask equipped with a football shaped magnetic stir bar was charged aldehyde (2.0 mmol, 1.0 equiv), (S)-tert-butanesulfinamide (291 mg, 2.4 mmol, 1.2 equiv) and THF (2.0 mL). The flask was sealed with a rubber septum and a nitrogen inlet needle was inserted in the septum. The reaction mixture was then treated dropwise with B(OCH2CF3)3 (0.43 mL, 2.0 mmol, 1.0 equiv) and the solution was stirred at rt for 2-6 h (until complete consumption of aldehyde by HPLC analysis at 220 nm). The reaction mixture was then diluted with EtOAc and the EtOAc solution was washed with saturated aqueous NaHCO3 solution followed by water. The organic phase was then dried over Na2SO4, filtered and concentrated to give the crude product. Purification by flash chromatography on SiO2 using hexanes/MTBE as eluent gave the pure product.
二、制备N-甲苯磺酰基亚胺
三、制备N-(二甲胺)磺酰基亚胺
四、N-二苯基次膦酰基亚胺
五、N-(α-甲基苄基)亚胺
