Table 1. Optimization of Reaction Conditionsa.
| entry | catalyst | oxidant | solvent | yieldb (%) | sel (%) |
|---|---|---|---|---|---|
| 1 | TBHP (1 equiv) | H2O | 24 | 88 | |
| 2 | TBHP (2 equiv) | H2O | 53 | 86 | |
| 3 | TBHP (3.2 equiv) | H2O | 89 | 97 | |
| 4 | TBHP (5.0 equiv) | H2O | 92 | 98 | |
| 5c | TBHP (3.2 equiv) | H2O | 32 | 93 | |
| 6d | TBHP (3.2 equiv) | H2O | 36 | 95 | |
| 7 | H2O2 (3.2 equiv) | H2O | 32 | 53 | |
| 8 | DTBP (3.2 equiv) | H2O | trace | ||
| 9 | urea peroxide (3.2 equiv) | H2O | trace | ||
| 10e | TBHP (3.2 equiv) | H2O | 83 | 91 | |
| 11 | TBHP (3.2 equiv) | toluene | 53 | 93 | |
| 12 | TBHP (3.2 equiv) | MeOH | 26 | 87 | |
| 13 | TBHP (3.2 equiv) | DMSO | 23 | 91 |
Unless otherwise specified, all of the reactions were carried out with benzyl alcohol (2.0 mmol, 208 μL) and 2-aminobenzamide (1.0 mmol, 136 mg) as the model substrates, illuminated under a 40 W white light-emitting diode (LED) lamp for 12 h at 25 °C.
Isolated yield.
Under dark conditions at 25 °C.
Under dark conditions at 90 °C.
Under a N2 environment.
