Optimization of the reaction conditionsa.
| |||
|---|---|---|---|
| Entry | Catalyst | Additive | Yieldb (%) |
| 1 | None | NaOAc | 15 |
| 2 | FeCl2 | NaOAc | 41 |
| 3 | Fe(acac)3 | NaOAc | 32 |
| 4 | CuBr | NaOAc | 11 |
| 5 | CuBr2 | NaOAc | Trace |
| 6 | PdCl2 | NaOAc | 36 |
| 7 | Pd(OAc)2 | NaOAc | 35 |
| 8 | Pd2(dba)3 | NaOAc | 40 |
| 9 | Pd(PPh3)2Cl2 | NaOAc | 60 |
| 10 | Pd(PCy3)2Cl2 | NaOAc | 43 |
| 11 | Pd(PPh3)2Cl2 | None | 10 |
| 12 | Pd(PPh3)2Cl2 | PivONa | 35 |
| 13 | Pd(PPh3)2Cl2 | PhCO2Na | 13 |
| 14 | Pd(PPh3)2Cl2 | NaOAc | Tracec |
| 15 | Pd(PPh3)2Cl2 | NaOAc | 67d |
Reaction conditions: 1b (0.3 mmol), 4a (0.2 mmol), catalyst (0 or 10 mol%), additive (0 or 1 equiv.), MeCN (2 mL), 60 °C, 12 h, in a sealed tube, under Ar.
Isolated yields; dr > 19 : 1.
Reaction was run at 40 °C.
NaOAc (0.5 equiv.) was used.