Optimization of the second step: solid-state ligand exchange of 3a with 2-phenylpyridine (2a) in the presence of silver salta.
| ||||
|---|---|---|---|---|
| Entry | Silver salt (2.0 equiv.) | Time (min) | Internal temp.b (°C) | Yield (%) of 4ac |
| 1 | AgOTf | 60 | 135 | 73 |
| 2 | None | 60 | 135 | 12 |
| 3 | AgOTf | 60 | 30 | 5 |
| 4 | AgOTf | 30 | 135 | 70 |
| 5 | Ag2O | 60 | 135 | 10 |
| 6 | Ag2CO3 | 60 | 135 | 14 |
Conditions: 3a (0.05 mmol), silver salt (0.10 mmol), 2a (0.25 mmol), 2-methoxyethan-1-ol (0.20 μL mg−1) in a stainless-steel milling jar (1.5 mL) with a stainless-steel ball (5 mm).
The reaction temperature was controlled using a heat gun (for details, see the ESI). The internal temperature was confirmed by thermography immediately after opening the milling jar.
Isolated yields are shown.