BENZYL-[1-(2,4-DICHLOROPHENYL)ETHYL]AMINE synthesis

Yield:259109-73-4 96 %

Reaction Conditions:

with bis(1,5-cyclooctadiene)diiridium(I) dichloride;BrettPhos;hydrogen in tetrahydrofuran;2,2,2-trifluoroethanol at 40; under 30402 Torr;Autoclave;

Steps:

General procedure for direct reductive amination.

General procedure: In a nitrogen-filled glovebox, [Ir(cod)Cl]2 (2.0 mg, 3 μmol) and PPh3 (3.5 mg, 13.2 μmol) were dissolved in anhydrous trifluoroethanol (2 mL) in a 10 mL vial equipped with a stir bar. The above solution was stirred at room temperature for 20 min to in situ generate the Ir-PPh3 complex. To a 5 mL vial equipped with a stir bar were added amine (0.3 mmol) and aldehyde (0.36 mmol) substrates, followed by the addition of anhydrous trifluoroethanol (1.5 mL) and the Ir-PPh3 complex solution (10 μL, 0.01 mol%). The resulting vial was transferred to an autoclave, which was purged with H2 3 times and then charged with H2 (20 atm), and stirred at room temperature for 24 h. The hydrogen gas was released slowly and the solution was concentrated to give the crude products, which were purified by column chromatography to afford the final product. For the reaction of ketones and amines, due to the low solubility of the Ir-BrettPhos and Ir-SPhos complexes in trifluoroethanol, tetrahydrofuran (THF) was instead used for the in situ generation of the catalyst.

References:

Wang, Jing;Wang, Wenji;Yang, Xiongyu;Liu, Jingwen;Huang, Haizhou;Chang, Mingxin [Science China Chemistry,2023,vol. 66,# 2,p. 518 - 525]