Table 2.
Entry | Solvent | Oxidant | Base | Amount of catalyst (mg) | Temperature () | Yielda (%) |
---|---|---|---|---|---|---|
1 | CH3CN | TBHP | CaCO3 | – | 80 | – |
2 | CH3CN | H2O2 | CaCO3 | – | 80 | – |
3 | CH3CN | – | CaCO3 | 10 | 80 | – |
4 | CH3CN | TBHP | CaCO3 | 10 | 25 | 23 |
5 | CH3CN | TBHP | CaCO3 | 10 | 60 | 47 |
6 | CH3CN | TBHP | CaCO3 | 10 | 80 | 72 |
7 | CH3CN | TBHP | CaCO3 | 20 | 80 | 89 |
8 | CH3CN | TBHP | CaCO3 | 20 | 100 | 73 |
9 | CH3CN | TBHP | CaCO3 | 30 | 80 | 89 |
10 | CH3CN | TBHP | K2CO3 | 20 | 80 | – |
11 | CH3CN | TBHP | Na2CO3 | 20 | 80 | – |
12 | CH3CN | H2O2 | CaCO3 | 20 | 80 | 32 |
13 | CH3CN | O2 | CaCO3 | 20 | 80 | 27 |
14 | DMF | TBHP | CaCO3 | 20 | 80 | 52 |
15 | DMSO | TBHP | CaCO3 | 20 | 80 | 67 |
Reaction conditions: benyzlamine hydrochloride (1.0 mmol), benzyl alcohol(1.5 mmol), catalyst, solvent (3.0 mL), base (1 mmol), oxidant(70 wt% in H2O, 4 equiv), under N2 atmosphere at 80 °C for 4 h.
aThe yields relate to the isolated product.