Table 2.
Condition optimization for the reaction of p-iodotoluene and benzeneboronic acid-catalyzed using the Ni(II)-β-CD complex.
| Entry | Catalyst (mol%Ni) | Base | Solvent | Yielda (%) |
|---|---|---|---|---|
| 1 | 2.5 | K2CO3 | THF | 5 |
| 2 | 2.5 | K2CO3 | Toluene | 7 |
| 3 | 2.5 | K2CO3 | CH3CN | 11 |
| 4 | 2.5 | K2CO3 | dioxane | 2 |
| 5 | 2.5 | K2CO3 | DMF | 4 |
| 6 | 2.5 | K2CO3 | EtOH | 35 |
| 7 | 2.5 | K2CO3 | MeOH | 21 |
| 8 | 2.5 | K2CO3 | DMSO | Trace |
| 9 | 2.5 | K2CO3 | H2O | 96 |
| 10 | 2.5 | K2CO3 | H2O | 41b |
| 11 | 0.5 | K2CO3 | H2O | 24 |
| 12 | 1 | K2CO3 | H2O | 50 |
| 13 | 1.5 | K2CO3 | H2O | 65 |
| 14 | 2 | K2CO3 | H2O | 79 |
| 15 | 2.5 | Cs2CO3 | H2O | 76 |
| 16 | 2.5 | Na2CO3 | H2O | 79 |
| 17 | 2.5 | DABCO | H2O | 8 |
| 18 | 2.5 | NEt3 | H2O | Trace |
| 19 | 2.5 | t‐BuOK | H2O | 55 |
Reaction status: phenylboronic acid, p-iodotoluene, base (with the ratio: 0.75:0.5:0.75), Ni(II)-β-CD complex, and solvent (1 mL) undergo Argon.
aYield determined by GC.
bThe reaction was conducted at ambient temperature.
Significant values are in bold.