Substrate scope using Cu@pNIPAM-VP.
| |||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Entry | Product | Cu(i)@pNIPAM-VPa | Cu(ii)@pNIPAM-VPb | Entry | Product | Cu(i)@pNIPAM-VPa | Cu(ii)@pNIPAM-VPb | ||||
| Time (h) | Isolated yield (%) | Time (h) | Isolated yield (%) | Time (h) | Isolated yield (%) | Time (h) | Isolated yield (%) | ||||
| 1 |
|
2 | 94 | 2 | 91 | 10 |
|
6 | 88 | 8 | 75 |
| 2 |
|
3 | 92 | 2 | 93 | 11d |
|
4 | 62 | 4 | 88 |
| 3 |
|
2 | 92 | 2 | 92 | 12 |
|
6 | 89 | 6 | 88 |
| 4 |
|
4 | 93 | 4 | 92 | 13d |
|
6 | 70 | 6 | 73 |
| 5c |
|
6 | 75 | 6 | 71 | 14 |
|
6 | 92 | 6 | 90 |
| 6 |
|
4 | 75 | 4 | 90 | 15 |
|
6 | 90 | 6 | 92 |
| 7 |
|
2 | 89 | 2 | 90 | 16 |
|
6 | 91 | 6 | 93 |
| 8 |
|
4 | 84 | 4 | 90 | 17 |
|
6 | 92 | 6 | 90 |
| 9d |
|
8 | 72 | 8 | 74 | ||||||
Reaction conditions: aryl bromide (1.0 mmol), aryl acetylene (1.0 mmol), sodium azide (1.0 mmol), Cu(i)@pNIPAM-VP (5 mol% of Cu), H2O (2 mL).
Cu(ii)@pNIPAM-VP (1.0 mol% of Cu).
4-Aminobenzyl azide was prepared by the reaction of 4-aminobenzyl bromide with sodium azide for 2 hours; phenyl acetylene was subsequently added to the reaction mixture.
Benzylbromide (1.2 mmol).