Table 1. Optimization of the Reaction Conditions for the Model Reactiona.
| entry | solvent | promoter | t (°C) | time (h) | yieldb (%) |
|---|---|---|---|---|---|
| 1 | CH3CN | reflux | 12 | nr | |
| 2 | CH3CN | AgOTf | reflux | 12 | nr |
| 3 | CH3CN | Cu(OTf)2 | reflux | 12 | nr |
| 4 | CH3CN | K2CO3 | reflux | 12 | 33 |
| 5 | CH3CN | Cs2CO3 | reflux | 12 | 62 |
| 6 | 1,4-dioxane | Cs2CO3 | reflux | 12 | 68 |
| 7 | 1,4-dioxane | t-BuOK | reflux | 12 | complex |
| 8 | CH3CN | DBU | reflux | 12 | 82 |
| 9 | 1,4-dioxane | DBU | reflux | 12 | nr |
| 10 | acetonec | DBU | reflux | 12 | 90 |
| 11 | EtOH | DBU | reflux | 12 | 12 |
| 12 | acetone | DABCO | reflux | 12 | nr |
| 13 | acetone | Et3N | reflux | 12 | nr |
| 14 | acetone | DBU | reflux | 8 | 85 |
| 15 | acetone | DBU | reflux | 16 | 89 |
Reaction conditions: 1a (1.1 mmol), 3a (1.0 mmol), base (2.0 mmol), solvent (15 mL).
Isolated yield based on 3a. nr = no reaction.
Bold entry indicates the best condition.
