Table 7 Comparison of catalytic activities of our catalyst with various reported bimetallic Pd catalysts for Mizoroki–Heck and Buchwald–Hartwig amination reactions.
Entryref | Coupling reaction | Catalyst: amount of Pd (mol %) | Reaction conditions | Ar-X | Time (h) | Yield (%) |
|---|---|---|---|---|---|---|
170 | Mizoroki–Heck | Pd63Sn37/C NPs (0.12) | DMF, Et3N, 140 °C | I | 6 | 98 |
Br | 43–95 | |||||
Cl | 65 | |||||
271 | Mizoroki–Heck | AuPd/Ni-Al-O (0.2) | DMF, K2CO3, 100 °C | I | 8 | 92 |
354 | Mizoroki–Heck | AuPd/Euphorbia condylocarpa M.bieb NPs(0.2) | H2O, K2CO3, 80 °C, CTAB | I | 8 | 89–95 |
572 | Mizoroki–Heck | ZnPd/phenanthroline (1) | DMF, K3PO4, 120 °C, TEAB | I | 24 | 96 |
673 | Mizoroki–Heck | Ni0.95Pd0.05 NPs (2) | DMF/H2O, K2CO3, 80 °C | I | 9–24 | 48–76 |
774 | Mizoroki–Heck | Pd50Ni50/MWCNTsa NPs (0.1) | H2O, KOH, 120 °C, TBAB | I | 1 | 99 |
855 | Mizoroki–Heck | PdNi/CL-HAb (0.4) | H2O, Bu3N, 120 °C, TBAB, N2 | I | 12 | 100 |
Br | 96–100 | |||||
Cl | 28–36 | |||||
108 | Mizoroki–Heck | PdCu/AOTc/iso-octane NPs (0.1) | DMF, Et3N, 100 °C | I | 18 | 93–100 |
Br | 74–97 | |||||
Cl | 66–85 | |||||
1175 | Mizoroki–Heck | Pd0.1Au0.16/Fe3O4@LDHd (0.05) | DMF/H2O, K2CO3, 120 °C | I | 0.67–2 | 89–99 |
Br | 2.5–24 | 43–98 | ||||
1276 | Mizoroki–Heck | Pd-M(M = Ag, Ni, and Cu)/C NPs (0.3) | Acetonitrile, Et3N, 82 °C | I | 3 | 35–62 |
1377 | Mizoroki–Heck | MnPd@Py-2,2′-BPyPh COF (0.08) | Acetonitrile, K2CO3, 80 °C, N2 | I | 24 | 95 |
1478 | Mizoroki–Heck | Hierarchical Pd–Ni/Ni(OH)2 (0.02) | TBAA, Et3N, 160 °C | I | 24 | 87 |
1511 | Mizoroki–Heck | Pd-Co/CoAl-LDH (0.02) | DMF/H2O, K2CO3, 120–140 °C | I | 0.5–1.5 | 91–100 |
Br | 4–5 | 92–93 | ||||
Cl | 10 | 64 | ||||
16This work | Mizoroki–Heck | γ-Fe2O3@MBD/Pd-Co NPs (0.05) | H2O, Et3N, 60 °C | I | 0.4–1.1 | 95–99 |
Br | 1.5–2 | 95–98 | ||||
Cl | 4–5 | 90–99 | ||||
1779 | Buchwald–Hartwig amination | PdAu/C (3) | DMSO, t-BuOK, 100 °C | Cl | 12 | 80–99 |
1867 | Buchwald–Hartwig amination | Pd–Ni/B-NPs (0.45) | K2CO3, H2O, 80 °C | Br | 5–8 | 86–100 |
Cl | 8 | 69–100 | ||||
19This work | Buchwald–Hartwig amination | γ-Fe2O3@MBD/Pd-Co NPs (0.05–0.07) | t-BuONa, H2O, 50–80 °C | I | 3.5–7.3 | 89–93 |
Br | 3.5–5 | 88–93 | ||||
Cl | 4.2–6 | 81–91 |