Study of reaction conditionsa.
| ||
|---|---|---|
| Entry | Variation from standard conditions | Yield of 3aa (%) |
| 1 | None | 73, 70b |
| 2 | Without CuCl2 | <10 |
| 3 | CuI instead of CuCl2 | 38 |
| 4 | Cu(OAc)2 instead of CuCl2 | 27 |
| 5 | CuBr2 instead of CuCl2 | 53 |
| 6 | FeCl3 instead of CuCl2 | 55 |
| 7 | nBu4NI instead of KI | 72 |
| 8 | NaI instead of KI | 64 |
| 9 | I2 instead of KI | 45 |
| 10 | Without KI | <10 |
| 11 | Under argon | 60 |
| 12 | DMF instead of DMSO | 25 |
| 13 | 1,4-Dioxane instead of DMSO | 30 |
| 14 | Toluene instead of DMSO | 31 |
Reaction conditions: 1a (0.1 mmol), 2a (0.05 mmol), CuCl2 (0.03 mmol), KI (0.05 mmol), DMSO (1 mL), 120 °C, 24 h, under air. Isolated yields.
5 mmol scale.