Figure 4

Hydrogenation of various unactivated amides. Unless otherwise specified, the reaction was performed using 1a (1 mol %), 3 (100 mol%), and NaH (6–10 mol %) in toluene. Pressure indicated is of H2 at 25 °C. nd: not determined. See Supplementary Information for experimental details. (a) Comparison of effects of steric bulkiness of 3 on reaction conditions. † 1a was preactivated: P H2(pre) = 1 MPa, T pre = 160 °C, t pre = 5 h. (b) Hydrogenation of CO2-derived 3. ‡1 mol % 1b preactivated was used instead of 1a: P H2(pre) = 8 MPa, T pre = 160 °C, t pre = 2 h.