Table 1. Optimization of Reaction Conditionsa.
entry | variation from the standard condition | yield of 6a/7 (%)b |
---|---|---|
1 | none | 80/4 |
2 | B instead of A | 25/22 |
3 | C instead of A | <1/19 |
4 | D instead of A | <1/27 |
5 | E instead of A | 27/34 |
6 | reaction at room temperature | 55/3 |
7 | Cs2CO3 instead of K2CO3 | 60/20 |
8 | NEt3 instead of K2CO3 | 50/40 |
9 | DBU instead of K2CO3 | 44/33 |
10 | 20 mol % of K2CO3, 10 mol % of NHC | 67/5 |
11 | 1 equiv of K2CO3 | 60/17 |
12 | CH3CN instead of THF | 10/26 |
13 | 1,4-dioxane instead of THF | 53/32 |
14 | toluene instead of THF | 20/15 |
15 | 1 equiv of 4a | 65/5 |
Reaction conditions: 5 (1.0 equiv, 0.35 mmol), 4a (1.5 equiv, 0.52 mmol), pre-NHC catalyst A (15 mol %), K2CO3 (50 mol%), solvent (2 mL), 4 h, under argon atmosphere.
Isolated yields.