Table 1. Optimization of the Reaction Conditionsa.
| entry | changes from the standard conditions | yield (%)b |
|---|---|---|
| 1 | none | 78 |
| 2 | KI (0.2 equiv) as the catalyst | trace |
| 3 | NaI (0.2 equiv) as the catalyst | trace |
| 4c | I2 (0.2 equiv) as the catalyst | 52 |
| 5 | TBAI (0.2 equiv) as the catalyst | 27 |
| 6 | NIS (0.2 equiv) as the catalyst | 47 |
| 7 | I2 (0.1 equiv) as the catalyst | 49 |
| 8 | I2 (0.3 equiv) as the catalyst | 53 |
| 9 | DMF as the solvent | 15 |
| 10 | MeCN as the solvent | 20 |
| 11 | NMP as the solvent | 43 |
| 12 | toluene as the solvent | trace |
| 13 | temp = 100 °C | 45 |
| 14 | temp = 140 °C | 50 |
| 15 | TBHP (2 equiv) | 52 |
| 16 | TBHP (4 equiv) | 60 |
| 17 | no catalyst | trace |
| 18 | no oxidant | trace |
Reactions were performed on a 0.3 mmol scale, 1a (0.3 mmol) and 2a (0.54 mmol.).
Isolated yield.
2 equiv of TBHP was used.
