Table 2. Optimization of [Pd]-Catalyzed Annulation.
entrya | catalyst | ligand | base | yieldc |
---|---|---|---|---|
9 | Pd(OAc)2 | dppf | K3PO4 | 65% |
10 | PdCl2 | dppf | K3PO4 | 16% |
11 | PdO | dppf | K3PO4 | 20% |
12 | Pd(OAc)2 | Xantphos | K3PO4 | 33% |
13b | Pd(OAc)2 | dppf | K3PO4 | 42% |
14 | Pd(OAc)2 | dppf | Cs2CO3 | 72% |
15 | Pd(OAc)2 | dppf | K2CO3 | 81% |
16 | PdCl2(PPh3)2 | K3PO4 | n.dd | |
17 | Pd(dppf)Cl2 | K3PO4 | 34% | |
18 | [(C6H5)3P]2Pd(CH2C6H5)Cl | K3PO4 | trace | |
19 | PdCl2·(CH3CN)2 | K3PO4 | trace |
Reaction conditions: 10a (0.5 mmol), catalyst (5 mol %), ligand (10 mol %), base (1 mmol), 1,4 dioxane (5 mL), reflux, overnight.
Microwave, 120 °C, 30 min.
Isolated yields.
Not detected.