Optimization for N-arylationa.
| ||||
|---|---|---|---|---|
| Entry | Base | Solvent | 3aa (%) | 4aa (%) |
| 1 | DIPEA | Toluene | 86 | 6 |
| 2 | n-Bu3N | Toluene | 85 | 4 |
| 3 | Et2NPh | Toluene | 88 | 6 |
| 4 | Me2NPh | Toluene | 77 | 3 |
| 5 | MeNPh2 | Toluene | 30 | 7 |
| 6 | Et2NPh | Dioxane | 83 | 4 |
| 7 | Et2NPh | DMA | 73 | 8 |
| 8 | Et2NPh | DMSO | 43 | 4 |
| 9 | Et2NPh | FPh | 90(90)b | Trace(trace)b |
| 10 | Et2NPh | ClPh | 85 | 6 |
| 11 | DIPEA | FPh | 81 | 4 |
| 12 | n-Bu3N | FPh | 75 | 6 |
Reaction conditions: 1a (0.5 mmol), Ph2IOTf (1.2 equiv.), base (2 equiv.), solvent (1 mL), 100 °C, 16 h.
85 °C.