Table 2 Optimization of the C–C amination providing primary anilines.
From: Hydroxylamine-mediated C–C amination via an aza-hock rearrangement
| |||
|---|---|---|---|
Entry | Reagent | Solvent | Yielda |
1 | 5a | HFIP | 28% |
2 | 5b | HFIP | 39% |
3 | 5c | HFIP | 20% |
4 | 5d | HFIP | 48% |
5 | 5e | HFIP | 50% |
6 | 5f | HFIP | 44% |
7 | 5g | HFIP | 48% |
8 | 5h | HFIP | trace |
9 | 5i | HFIP | trace |
10 | 5j | HFIP | 10% |
11 | 5k | HFIP | n.d. |
12 | 5l | HFIP | 16% |
13 | 5m | HFIP | 59% |
14 | 5n | HFIP | 41% |
15 | 5o | HFIP | 33% |
16 | 5p | HFIP | n.d. |
17 | 5q | HFIP | 17% |
18 | 5r | HFIP | n.d. |
19 | 5s | HFIP | 44% |
20 | 5t | HFIP | 48% |
21 | 5u | HFIP | 36% |
22 | 5m | TFE | 63% |
23 | 5m (1.3 eq) | TFE | 72% |
24 | 5m (1.5 eq) | TFE | 84% (79%b) |
25 | 5m (1.5 eq) | TFE (0.4 M) | 72% |
