Table 1 The effect of halide anions on liquid-phase HDH of HACs over 5% Pd/C and Raney Ni catalysts in ethanol-water (50/50, v/v).
Entry | Catalyst | HAC a | halide anion | Time (min) | Conversion (%) b | Conversion rate (mmol L−1 min−1) | factor c |
|---|---|---|---|---|---|---|---|
1 | Pd/C | 4-CP | no | 40 | 100 | 0.500 | – |
2 | F− | 40 | 100 | 0.500 | 1.0 | ||
3 | Cl− | 40 | 100 | 0.500 | 1.0 | ||
4 | Br− | 40 | 100 | 0.500 | 1.0 | ||
5 | I− | 40 | 13.9 | 0.070 | 7.1 | ||
6 | 4-BP | no | 10 | 100 | 2.000 | – | |
7 | F− | 10 | 100 | 2.000 | 1.0 | ||
8 | Cl− | 10 | 100 | 2.000 | 1.0 | ||
9 | Br− | 10 | 100 | 2.000 | 1.0 | ||
10 | I− | 10 | 97.3 | 0.408 | 4.9 | ||
11 | 4-IP | no | 90 | 57.8 | 0.128 | – | |
12 | F− | 90 | 56.7 | 0.126 | 1.0 | ||
13 | Cl− | 90 | 57.9 | 0.129 | 1.0 | ||
14 | Br− | 90 | 57.5 | 0.128 | 1.0 | ||
15 | I− | 90 | 44.2 | 0.098 | 1.3 | ||
16 | Raney Ni | 4-CP | no | 25 | 100 | 0.800 | – |
17 | F− | 25 | 99.1 | 0.793 | 1.0 | ||
18 | Cl− | 25 | 99.2 | 0.794 | 1.0 | ||
19 | Br− | 25 | 99.2 | 0.794 | 1.0 | ||
20 | I− | 25 | 86.5 | 0.346 | 2.3 | ||
21 | 4-BP | no | 20 | 100 | 1.000 | – | |
22 | F− | 20 | 100 | 1.000 | 1.0 | ||
23 | Cl− | 20 | 100 | 1.000 | 1.0 | ||
24 | Br− | 20 | 100 | 1.000 | 1.0 | ||
25 | I− | 20 | 95.3 | 0.953 | 1.1 | ||
26 | 4-IP | no | 15 | 100 | 1.333 | – | |
27 | F− | 15 | 100 | 1.333 | 1.0 | ||
28 | Cl− | 15 | 100 | 1.333 | 1.0 | ||
29 | Br− | 15 | 100 | 1.333 | 1.0 | ||
30 | I− | 15 | 80.8 | 1.077 | 1.2 |
- aReaction conditions: solvent (80 mL), each HAC (1.6 mmol), NaOH (0.0704 g, 1.76 mmol), halide anion (1.0 mmol), 5% Pd/C (20 mg), Raney Ni (0.12 g), temperature (30 °C), H2: 10 mL min−1.
- bProducts and yields were determined by GC-MS and GC-FID.
- c
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