Optimization of the reaction conditionsa.
| ||||
|---|---|---|---|---|
| Entry | Cat. | Base | Solvent | Yield |
| 1 | Ni(PPh3)2Cl2 | Cs2CO3 | DMF | 67% |
| 2 | Pd(OAc)2 | Cs2CO3 | DMF | 65% |
| 3 | Cu(OAc)2 | Cs2CO3 | DMF | 65% |
| 4 | Co(OAc)2 | Cs2CO3 | DMF | 63% |
| 5 | Cs2CO3 | DMF | 65% | |
| 6 | KF | DMF | Trace | |
| 7 | K3PO4 | DMF | Trace | |
| 8 | K2CO3 | DMF | 48% | |
| 9 | KOH | DMF | 52% | |
| 10 | KOtBu | DMF | 46% | |
| 11 | Et3N | DMF | Trace | |
| 12 | Cs2CO3 | CH3CN | 18% | |
| 13 | Cs2CO3 | DME | 23% | |
| 14 | Cs2CO3 | Toluene | Trace | |
| 15 | Cs2CO3 | DCE | Trace | |
| 16 | Cs2CO3 | Dioxane | Trace | |
Reaction conditions: 1a (0.1 mmol, 1 equiv.), TMSCN (0.3 mmol, 3 equiv.), cat. (0 or 10 mol%), base (0.3 mmol, 3 equiv.) and solvent (1 mL), at 80 °C for 10 h; isolated yield.