Optimization of the reaction conditionsa,b.
| |||||
|---|---|---|---|---|---|
| Entry | Cat. | P ligand | Base | Solvent | Yieldb (%) |
| 1 | PdCl2 | XPhos | K3PO4 | DMF | 40 |
| 2 | Pd2(dba)3 | XPhos | K3PO4 | DMF | 10 |
| 3 | Pd(dppf)Cl2 | XPhos | K3PO4 | DMF | 35 |
| 4 | Pd(PPh3)2Cl2 | XPhos | K3PO4 | DMF | 10 |
| 5 | Pd(acac)2 | XPhos | K3PO4 | DMF | 19 |
| 6 | Pd(OAc)2 | XPhos | K3PO4 | DMF | 58 |
| 7 | Pd(OAc)2 | dppe | K3PO4 | DMF | 5 |
| 8 | Pd(OAc)2 | PPh3 | K3PO4 | DMF | 6 |
| 9 | Pd(OAc)2 | dppp | K3PO4 | DMF | 15 |
| 10 | Pd(OAc)2 | JohnPhos | K3PO4 | DMF | 20 |
| 11 | Pd(OAc)2 | SPhos | K3PO4 | DMF | 32 |
| 12 | Pd(OAc)2 | Ruphos | K3PO4 | DMF | 30 |
| 13 | Pd(OAc)2 | XPhos | K2HPO4 | DMF | 50 |
| 14 | Pd(OAc)2 | XPhos | Cs2CO3 | DMF | 23 |
| 15 | Pd(OAc)2 | XPhos | NaHCO3 | DMF | 25 |
| 16 | Pd(OAc)2 | XPhos | Et3N | DMF | 21 |
| 17 | Pd(OAc)2 | XPhos | K3PO4 | DMSO | 43 |
| 18 | Pd(OAc)2 | XPhos | K3PO4 | DMA | 31 |
| 19 | Pd(OAc)2 | XPhos | K3PO4 | Dioxane | Trace |
| 20 | Pd(OAc)2 | XPhos | K3PO4 | MeCN | 58 |
| 21 | Pd(OAc)2 | XPhos | K3PO4 | EtOH | 46 |
| 22 | Pd(OAc)2 | XPhos | K3PO4 | iPrOH | 72 |
| 23 | Pd(OAc)2 | XPhos | K3PO4 | tAmOH | 63 |
| |||||
1a (0.36 mmol), 2a (0.30 mmol), cat. Pd (5 mo%), ligand (5 mo%), base (0.3 mmol), solvent (2.0 mL), 80 °C, 16 h, under N2.
Isolated yield.