Table 3 C–C coupling of iodobenzene with phenylboronic acid in the presence of Pd-BisPyP@bilayer-SiO2@NMP under various conditionsa.
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|---|---|---|---|---|---|---|
Entry | Solvent | Base (mmol) | Temperature (°C) | Catalyst (mg) | Time (min) | Yield (%)b |
1 | 1,4-Dioxane | Na2CO3 | 70 | 5 | 5 | – |
2 | EtOH | Na2CO3 | Reflux | 5 | 5 | 26 |
3 | H2O | Na2CO3 | 70 | 5 | 5 | 22 |
4 | DMSO | Na2CO3 | 70 | 5 | 5 | 69 |
5 | DMF | Na2CO3 | 70 | 5 | 5 | 72 |
6 | PEG | Na2CO3 | 70 | 5 | 5 | 98 |
7 | PEG | Et3N | 70 | 5 | 5 | 24 |
8 | PEG | DMAP | 70 | 5 | 5 | 27 |
9 | PEG | KOH | 70 | 5 | 5 | 64 |
10 | PEG | NaOH | 70 | 5 | 5 | 47 |
11 | PEG | NaHCO3 | 70 | 5 | 5 | 85 |
12 | PEG | – | 70 | 5 | 240 | — |
13 | PEG | Na2CO3 | 25 | 5 | 180 | — |
14 | PEG | Na2CO3 | 50 | 5 | 60 | 57 |
15 | PEG | Na2CO3 | 90 | 5 | 5 | 98 |
16 | PEG | Na2CO3 | 70 | 4 | 60 | 79 |
17 | PEG | Na2CO3 | 70 | 6 | 5 | 98 |
18 | PEG | Na2CO3 | 70 | – | 1440 | – |
