Bis(1,5-cyclooctadiene)nickel(0) (Wax encapsulated) (ca. 0.05mmol/capsule)

A vial containing a magnetic stir bar is flame-dried under reduced pressure, and then allowed to cool under N₂. The vial is charged with morpholine (52.4 µL, 0.600 mmol, 1.2 equiv), sulfamate (100.5 mg, 0.500 mmol, 1.0 equiv), anhydrous powdered NaOtBu (72.0 mg, 0.750 mmol, 1.5 equiv), SIPr·HCl (42.7 mg, 0.100 mmol, 20 mol%), and a paraffin capsule containing Ni(cod)₂ (13.8 mg, 0.050 mmol, 10 mol%). The vial is flushed with N₂, and subsequently 1,4-dioxane (2.5 mL, 0.20 M) is added. The vial is capped with a Teflon-lined screw cap under a flow of N₂ and the reaction mixture is stirred at 80 °C for 3 h. After removing the vial from heat, the reaction mixture is transferred to a 100 mL round bottom flask containing 3.0 g of silica gel with hexanes (6.0 mL) and CH₂Cl₂ (6.0 mL). The mixture is adsorbed onto the silica gel under reduced pressure and filtered over a plug of silica gel (100 mL of hexanes eluent to remove paraffin, then 100 mL of 1:1 Hexanes:EtOAc eluent). The volatiles are removed under reduced pressure, and the crude residue is purified by preparative thin-layer chromatography (19:1 PhH:EtOAc) to yield amine (78% yield, average of two experiments) as a white solid.¹⁾