Synthesis of Cu-MOF-catalysed 1,4-disubstituted-1,2,3-triazole derivativesa.
| |||||||
|---|---|---|---|---|---|---|---|
| Entry | R1 | R2 | Product | [Cu(INA)2(H2O)4]-complex | Cu(INA)2-MOF | ||
| Time | Yieldb (%) | Time (h) | Yieldb (%) | ||||
| 1 | PhCH2, 1a | Ph, 2a |
|
12 min | 93 | 4 min | 95 |
| 2 | 1a | 4-OMeC6H4, 2b |
|
5 min | 85 | 4 min | 90 |
| 3 | 1a | 4-MeC6H4, 2c |
|
6 min | 81 | 5 min | 90 |
| 4 | 1a | 1-Naphthyl, 2d |
|
1 h | 97 | 1 h | 95 |
| 5 | 1a | 4-NH2C6H4, 2e |
|
10 min | 70 | 10 min | 96 |
| 6 | 4-OMeC6H4, 1b | 2a |
|
10 min | 86 | 10 min | 92 |
| 7 | 1b | 2e |
|
40 min | 70 | 40 min | 90 |
| 8 | 1b | 2c |
|
— | — | 1 h | 95 |
| 9 | 1a | PhCH2Se, 2f |
|
2 h | 80 | 2 h | 86 |
| 10 | 1a | PhSe, 2g |
|
1.5 h | 96c | 1.5 h | 98 |
| 11 | 1a | PhSeCH2, 2h |
|
12 h | 50 | 12 h | 70 |
Reaction conditions: azide (0.5 mmol), acetylene (0.5 mmol), catalyst (1 mol%).
Isolated yield.
A mixture of 1 : 1.4 ratio of the 1,4- and 1,5-regioisomers determined by 1H NMR spectroscopy.