Optimization of reaction conditions.
| ||
|---|---|---|
| Entrya | Deviation from standard conditions | Yieldb (%) |
| 1 | None | 85(82)c |
| 2 | CuCl (20 mol%) | 84 |
| 3 | CuCl (5 mol%) | 76 |
| 4 | No CuCl | 0 |
| 5 | CuI instead of CuCl | 70 |
| 6 | Cu2O instead of CuCl | 45 |
| 7 | CuBr instead of CuCl | 58 |
| 8 | Cu(OAc)2 instead of CuCl | 61 |
| 9 | Cu(OTf)2 instead of CuCl | 49 |
| 10 | L15 (40 mol%) | 79 |
| 11 | No L15 | 5 |
| 12 | No K3PO4 | 10 |
| 13 | DMSO instead of 1,4-dioxane | 13 |
| 14 | DMF instead of 1,4-dioxane | 10 |
| 15 | Toluene instead of 1,4-dioxane | 50 |
| 16 | H2O instead of 1,4-dioxane | 0 |
| 17 | EtOH instead of 1,4-dioxane | 38 |
| 18 | 90 °C instead of 125 °C | 67 |
| 19 | Air instead of N2 | 10 |
The general conditions are as follows: 1a (2.0 mmol), CuCl (0.1 mmol), L15 (0.2 mmol), K3PO4 (3.0 mmol), 1,4-dioxane (3.0 mL).
Determined by gas chromatography using n-decane as the internal standard.
Isolated yield.