Optimization of reaction conditions for the model reactiona.
| Entry | Catalysts | Time (h) [t1 + t2] | Solvent | Base | Yieldb (%) |
|---|---|---|---|---|---|
| 1 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 15 | CH3CN | K2CO3 | 34 |
| 2 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 15 | DMF | K2CO3 | 41 |
| 3 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 15 | H2O | K2CO3 | 54 |
| 4 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 15 | H2O | TEA | 91 |
| 5 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 5 | H2O | TEA | 51 |
| 6 | Pd(ii)/Cu(ii)@TADP–COF | 6 + 10 | H2O | TEA | 85 |
| 7 | Cu(ii)@TADP–COF | 6 + 15 | H2O | TEA | 0 |
| 8 | Pd(ii)@TADP–COF | 6 + 15 | H2O | TEA | 8 |
a
Reactions conditions: a mixture of 4-iodobenzyl alcohol (0.2 mmol), phenylboronic acid (1.5 equiv.), base (3.0 equiv.), TEMPO (0.25 equiv.), H2O (2.0 mL), catalyst (4 mg) was stirred at 60 °C under N2 (1.0 atm) for 6 h, and then O2 atmosphere (balloon pressure) was introduced and the reaction continued at 80 °C for another 15 h.
b
Determined by GC using tridecane as an internal standard.