Table 3.
entry | R1 | alkyne | product | time (h) | yield (%)b |
---|---|---|---|---|---|
1c | 4-BrC6H4 | 13 | 3 | 86 | |
2 | 4-BrC6H4 | 23 | 4.5 | 78 | |
3d | 4-H3COC6H4 | 14 | 6.5 | 94 | |
4 | 4-H3COC6H4 | 24 | 7 | 79 | |
5 | Bn | 25 | 3.5 | 87 | |
6e | Me | 26 | 12 | 88 | |
7e | i-Pr | 27 | 12 | 75 | |
8 | n-C8H17 | 28 | 3.5 | 92 | |
9f | 29 | 8.5 | 90 | ||
10g | 30 | 3 | 82 | ||
11g | 31 | 3 | 83 |
1.0 mmol scale unless otherwise noted; CuTC (10 mol %), solvent (0.2 M), alkyne (1 equiv), sulfonyl azide (1 equiv), rt.
Isolated yield.
5.0 mmol scale.
1.1 equiv alkyne.
1.3 equiv alkyne.
2.4 equiv alkyne.
1.2 equiv alkyne.