Table 8. Comparison with Reported Results for Suzuki–Miyaura Cross-Coupling Reactions between Phenylboronic Acid and 4-Methoxyphenyl Carbamates or Sulfamates.
| entry | X | catalyst | reaction conditions | time | yield (%) | reusability | refs |
|---|---|---|---|---|---|---|---|
| 1 | CONEt2 | triazine-based Ni(II) PNP pincer complexes (2 mol %) | toluene/K3PO4/120–135 °C | 16 h | 84 | (65) | |
| 2 | CONEt2 | NiCl2(PCy3)2 (10 mol %) | toluene/K3PO4/110 °C | 24 h | 41 | (66) | |
| 3 | SO2NMe2 | NiCl2(PCy3)2 (10 mol %) | toluene/K3PO4/110 °C | 24 h | 80 | (66) | |
| 4 | SO2NMe2 | dppf Ni(II) (o-tol) (Cl) (2.5 mol %) | toluene/K3PO4/80 °C | 24 h | 72 | (52) | |
| 5 | CONEt2 | Ni(PCy3)2Cl2 (5 mol %) | toluene/K3PO4/MW, 180 °C | 10 min | 67 | (67) | |
| 6 | SO2NMe2 | Ni(PCy3)2Cl2 (5 mol %) | toluene/K3PO4/MW, 180 °C | 10 min | 70 | (67) | |
| 7 | SO2NMe2 | NiCl2(dppp) (2 mol %) | dioxane/K3PO4/110 °C | 24 h | 35 | (68) | |
| 8 | SO2NMe2 | NiCl2(dppf) (5 mol %) | toluene/K3PO4/110 °C | 24 h | 68 | (69) | |
| 9 | CONMe2 | NiCl2(dppf) (5 mol %) | toluene/K3PO4/110 °C | 24 h | 19 | (69) | |
| 10 | CONEt2 | Fe3O4@SiO2–EDTA–Ni(II)(1 mol %) | EG/NaOC2H4OH/100 °C | 6 | 86 | Yes | this work |
| 11 | SO2NMe2 | Fe3O4@SiO2–EDTA–Ni(II)(1 mol %) | EG/NaOC2H4OH/100 °C | 6 | 87 | Yes | this work |