Table 1. Experiments for the Light-Mediated Cross-Coupling between Potassium Benzyltrifluoroborates and Aryl Bromidesa.
| entry | catalyst | yield (%)b | TON (Ir/Ni) |
|---|---|---|---|
| 1 | Ir,Ni@Phen-COF (1.2 mg, 4.0% Ir, 2.8% Ni) | 90 | 270/118 |
| 2 | Phen-COF (1.2 mg) | 0 | |
| 3 | No Catalyst | 0 | |
| 4 | Ir,Ni@Phen-COF (1.2 mg) (dark) | 0 | |
| 5 | PF–CrystallineLaminar COF (1.2 mg) | 0 | |
| 6 | Ni@Phen-COF (1.2 mg) | 0 | |
| 7 | Ir@Phen-COF (1.2 mg) | 0 | |
| 8 | Ni@Phen-COF (0.6 mg) | ||
| Ir@Phen-COF (0.6 mg) | 0 | ||
| 9 | [Ir(dF(CF3)ppy)2(bpy)]PF6 (0.3 mol %) [NiCl2(phen)] (0.7 mol %) | 23 | 69/30 |
| 10 | Ir,Ni@Phen-COF (1.2 mg, 7.0% Ir, 4.2% Ni) | 87 | 149/76 |
| 11 | Ir,Ni@Phen-COF (1.2 mg, 2.0% Ir, 1.4% Ni) | 25 | 150/66 |
| 12 | Ir,Ni@Phen-COF (1.2 mg, 2.2% Ir, 2.8% Ni) | 42 | 229/55 |
| 13 | Ir,Ni@Phen-COF (1.2 mg, 9.0% Ir, 2.8% Ni) | 46 | 61/60 |
The reaction was carried out using 2a (0.15 mmol), 3a (0.075 mmol), 2,6-lutidine (0.26 mmol), the corresponding catalyst, and 1 mL of solvent under an Ar atmosphere and blue light irradiation (blue LEDs, 23 W, 450 nm).
The yield was determined by 1H NMR using nitromethane as the internal standard.
