Reaction of styrene episulfide with phenylacetylene and sodium azide catalysed by Fe3O4@SiO2–PMA–Cu under different conditions.
Entry | Amount of catalyst (mg) | Solvent | Temperature (°C) | Time (min) | Yieldab (%) |
---|---|---|---|---|---|
1 | — | EtOH | Reflux | 10 | 0 |
2 | 2 | EtOH | Reflux | 15 | 43 |
3 | 3 | EtOH | Reflux | 15 | 75 |
4 | 5 | EtOH | Reflux | 15 | 81 |
5 | 8 | EtOH | Reflux | 15 | 94 |
6 | 10 | EtOH | Reflux | 15 | 98 |
7 | 12 | EtOH | Reflux | 15 | 100 |
8 | 15 | EtOH | Reflux | 15 | 100 |
9 | 12 | MeOH | Reflux | 15 | 95 |
10 | 12 | H2O | 80 | 15 | 93 |
11 | 12 | CH3CN | Reflux | 15 | 81 |
12 | 12 | DMF | 80 | 15 | 67 |
13 | 12 | EtOAc | Reflux | 15 | 73 |
14 | 12 | THF | Reflux | 15 | Trace |
15 | 12 | n-Hexane | Reflux | 15 | 28 |
16 | 12 | CCl4 | Reflux | 15 | 17 |
17 | 12 | Solvent free | 80 | 15 | Trace |
18 | 12 | EtOH | 25 | 15 | Trace |
19 | 12 | EtOH | 40 | 15 | 57 |
20 | 12 | EtOH | 60 | 15 | 76 |
21 | 12 | EtOH | 65 | 15 | 84 |
22 | 12 | EtOH | 70 | 15 | 93 |
Reaction conditions: phenylacetylene (1 mmol), episulfide (1 mmol) and sodium azide (1.3 mmol) catalyst (mg) and solvent (10 mL).
Isolated yields.