Table 1. Catalyst Optimization Studies for the Formation of Aniline 2aa.
| entry | catalyst (mol %) | time | yield 2a(%)b |
|---|---|---|---|
| 1 | ZnO (2.5 mol %) | 12 h | c |
| 2 | Zn0.7Mn0.3O2−δ (2.5 mol %) | 12 h | c |
| 3 | Zn0.7Fe0.3O2−δ (2.5 mol %) | 12 h | c |
| 4 | NiFe2O4 (2.5 mol %) | 12 h | c |
| 5 | CuFe2O4 (2.5 mol %) | 12 h | c |
| 6 | SnO2 (2.5 mol %) | 12 h | c |
| 7 | TiO2 (2.5 mol %) | 12 h | c |
| 8d | Pd/C (2.5 mol %) | 1 h | 46 |
| 9 | Pd/TiO2 (0.1 mol %) | 15 min | 82 |
| 10 | Au/TiO2 (0.1 mol %) | 10 min | 80 |
| 11 | Pd–Au/TiO2 (0.1 mol %) | 5 min | 96 |
Reaction conditions: nitrobenzene (1 mmol), hydrazine monohydrate (0.5 mL), and catalyst.
Isolated yields of product 2a.
Starting material 1a recovered.
Pd/C (palladium on activated charcoal).
