Comparison of activity for different catalytic systems in the coupling of benzyl alcohol and benzyl amine.
| Entry | Catalyst | Reaction condition | Yield (compound 3a or 4a) | Ref. no. |
|---|---|---|---|---|
| 1 | Au6Pd/resin | NaOH (1.1 eq.), O2 balloon, H2O, r.t., 2 h | 51% (3a) | 48 |
| 2 | Ru(COD)Cl2/PCyp3.HBF4 | KOtBu, toluene, 110 °C, 24 h | 78% (3a) | 49 |
| 3 | Cu2O/CQDs | CH3CN, O2, white cold LED λ > 400 nm, 24 h | 95% (4a) | 50 |
| 4 | Co2(CO)8/trioctylphosphine oxide (TOPO) | Mesitylene, 164 °C, 24 h | 79% (4a) | 51 |
| 5 | Silicagel supported salicylic acid | O2 (0.1 MPa), toluene, 90 °C, 24 h | 81% (4a) | 52 |
| 6 | Manganese pincer complex | KOtBu, toluene, 110 °C, 48 h | 88% (3a) | 53 |
| 7 | Cu-MOF | TBHP, THF, r.t | 86% (3a), 75% (4a) | Present work |