Table 2. Direct Synthesis of Primary Amines from Vanillyl Alcohol and (NH4)2CO3 Using Ni/Al2O3–SiO2 As a Catalysta.
| selectivity/% |
|||||||||
|---|---|---|---|---|---|---|---|---|---|
| entry | catalyst amount/mg | sub. (mmol)/(NH4)2CO3 (mmol) ratio | conversion /% | 2m | 5m | 4m | 6m | 3′m | dimers |
| 1 | 100 | 0.5:1 | 83 | 52 | 2 | 3 | 0 | 19 | 23 |
| 2 | 100 | 0.25:1 | 87 | 54 | 0 | 2 | 1 | 25 | 27 |
| 3 | 100 | 0.5:2 | 54 | 50 | 1 | 2 | 0 | 23 | 23 |
| 4 | 200 | 0.5:2 | >99 | 58 (40)b | 2 | 4 | 0 | 16 | 20 |
| 5 | 50 | 0.5:2 | 34 | 56 | 1 | 2 | 0 | 19 | 22 |
| 6 | 400 | 1:4 | >99 | 4 | 4 | 55 | 1 | 7 | 29 |
General reaction conditions: general procedure 2, Ni/Al2O3–SiO2 catalyst, vanillyl alcohol substrate, (NH4)2CO3, 3 mL t-amyl alcohol, 140 °C, 18 h; conversion and selectivity were calculated by GC-FID.
Isolated yield by column chromatography.
