Table 3. Conditions’ Optimization of the Model Heck Reaction between Iodobenzene and Styrenea.
entry | solvent | base | catalyst (mol %) | yield (%) |
---|---|---|---|---|
1 | ACN | Et3N | 0.34 | 11 |
2 | EtOH | Et3N | 0.34 | trace |
3 | EtOH/H2O (v/v, 2:1) | Et3N | 0.34 | trace |
4 | toluene | Et3N | 0.34 | 5 |
5 | DMF | Et3N | 0.34 | 80 |
6 | DMF/H2O (v/v, 2:1) | Et3N | 0.34 | 20 |
7 | DMF | K2CO3 | 0.34 | 70 |
8 | DMF | Na2CO3 | 0.34 | 59 |
9 | DMF | NaOAc | 0.34 | 44 |
10 | DMF | NaHCO3 | 0.34 | 50 |
11 | DMF | KOH | 0.34 | 6 |
12 | DMF | Et3N | 0 | 0 |
13 | DMF | Et3N | 0.50 | 85 |
14 | DMF | Et3N | 0.80 | 90 |
15 | DMF | Et3N | 1.00 | 99 |
16 | DMF | Et3N | 1.50 | 95 |
Conditions: 0.5 mmol iodobenzene, 0.75 mmol styrene, 1 mmol base, 120 °C, 7 h.