Catalytic Hydrogenation of Acetophenone

Inside the glovebox, a stock solution of 3 (0.0125 M) was prepared in 0.875 mL dioxane, treated with 0.125 mL of 1 M KBHEt₃ solution in THF and stirred for 0.5 h. A 1 mL syringe was loaded with complex 3 (500, 250, 100, and 50 μL) and KBHEt₃ (62.5, 93.8, 112.5, and 118.8 μL) in dioxane (total volume 0.7 mL), and a 20 mL syringe was loaded with acetophenone (1.460 mL, 12.5 mmol) and dodecane (113.6 μL, 0.625 mmol) in 10 mL dioxane. Under N₂ flow, the substrate syringe was first injected into high pressure stainless steel reactor, in which a glass liner was inserted in advance. The dissolved catalyst was then placed in an injection port and the system was purged with H₂ (3 × 10 bar). The reactor was brought to at 120 °C at 50 bar H₂ pressure with stirring at 500 r.p.m. and reaction was initiated by injecting the catalyst solution. The samples were withdrawn at given time intervals using an autosampler apparatus and analyzed with GC. Data plotted in Fig. 4 of the manuscript.