Table 2. GC Yields [%]a in Suzuki–Miyaura and Heck Cross-Coupling Reactions Catalyzed by Pd(II) Complexes Based on Ligands L1–L12.
GC yield [%] in Suzuki–Miyaura couplingb |
GC yield
[%] in Heck couplingc |
||||||
---|---|---|---|---|---|---|---|
pKa of L | PdL2Cl2 (1a–12a) | PdL2(NO3)2 (1b–12b) | PdL4(NO3)2 (1c–12c) | PdL2Cl2 (1a–12a) | PdL2(NO3)2 (1b–12b) | PdL4(NO3)2 (1c–12c) | |
L1 | 5.23 | 97 | 93 | 95 | 85 | 88 | 90 |
L2 | 5.98 | 93 | 92 | 98 | 90 | 91 | 94 |
L3 | 6.47 | 93 | 91 | 91 | 86 | 82 | 76 |
L4 | 3.49 | 78 | 72 | 64 | 89 | 92 | 79 |
L5 | 3.57 | 86 | 87 | 88 | 80 | 92 | 75 |
L6 | 9.61 | 93 | 90 | 86 | 83 | ||
L7 | 3.83 | 82 | 74 | 75 | 90 | 92 | 80 |
L8 | 2.10 | 88 | 66 | 91 | 93 | ||
L9 | 2.46 | 87 | 70 | 81 | 91 | ||
L10 | 3.07 | 98 | 90 | 93 | 88 | ||
L11 | 3.12 | 86 | 79 | 88 | 90 | ||
L12 | 2.86 | 83 | 92 | 92 | 77 |
Reaction yields were determined by GC–MS measurement of 4′-bromoacetophenone or iodobenzene decay as the average of three results.
Reaction conditions: 4′-bromoacetophenone (0.2 mmol, 1 equiv), phenylboronic acid (0.24 mmol, 1.2 equiv), K3PO4 (0.4 mmol, 2 equiv), and Pd(II) complex (0.1 mol %) were stirred in toluene (2 mL) at 80 °C for 2 h.
Reaction conditions: iodobenzene (0.2 mmol, 1 equiv), styrene (0.24 mmol, 1.2 equiv), Et3N (1.0 mmol, 5 equiv), and Pd(II) complex (0.1 mol %) were stirred in DMSO (2 mL) at 120 °C for 2 h.