Optimization studiesa.
| ||||
|---|---|---|---|---|
| Entry | Catalyst | Solvent | Temp. (°C) | 8 yield (%) |
| 1 | 10 | THF | 80 | 67 |
| 2 | 11 | THF | 80 | 53 |
| 3 | FeCl3 | DCE | rt | 0 |
| 4 | FeCl3 | DCE | 80 | 0 |
| 5 | TFA | THF | 80 | 0b |
| 6 | 10 | i-PrOH | 80 | 31 |
| 7 | 10 | CH3CN | 80 | 28 |
| 8 | 10 | EtOAc | 80 | 26 |
| 9 | 10 | Toluene | 80 | 24 |
| 10 | 10 | THF | 90 | 87 |
| 11 | 10 | THF | 100 | 96c |
| ||||
Conditions: substrate 8 (0.2 mmol) and 5 mol% catalyst in 0.4 mL of solvent (0.5 M) in a 5 mL sealed tube were heated to the temperature indicated for 15 h. Yields were determined by 1H NMR using CH2Br2 as an internal standard.
2 equiv. of TFA was used.
85% isolated yield.