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. 2022 Jun 16;12(28):17905–17918. doi: 10.1039/d2ra02587f

Reaction of styrene episulfide with phenylacetylene and sodium azide catalysed by Fe3O4@SiO2–PMA–Cu under different conditions.

graphic file with name d2ra02587f-u1.jpg
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
a

Reaction conditions: phenylacetylene (1 mmol), episulfide (1 mmol) and sodium azide (1.3 mmol) catalyst (mg) and solvent (10 mL).

b

Isolated yields.