Table 1.
Selective aerobic oxidation of benzyl alcohol (1a) to benzaldehyde (2a)a
| Entry | Catalyst | Yield (%) | Particle size (nm) | |
|---|---|---|---|---|
| Before use | After use | |||
| 1 | Au-TOASiW9 | 75 | 2.9 | 2.8 |
| 2 | Au-TOASiW9b | 92 | 2.9 | 2.9 |
| 3 | Au-TOASiW10 | 17 | 3.4 | 3.3 |
| 4 | Au-TOASiW11 | 24 | 2.9 | 3.0 |
| 5 | Au-TOASiW12 | 4 | 3.2 | 4.3 |
| 6 | Au-TOAB | 3 | 2.5 | 5.6 |
| 7 | Au-dodecanethiol | <1 | 2.6 | 2.7 |
| 8 | Au-dodecanethiolb | <1 | 2.6 | Precipitationc |
| 9 | TOASiW9 | <1 | – | – |
| 10 | Au-TOASiW9, Ard | <1 | 2.9 | − |
aReaction conditions: 1a (0.25 mmol), 3 mL toluene solution of colloidal gold nanoparticles (Au: 4 mol%), K2CO3 (0.5 mmol), room temperature (~25 °C), O2 (1 atm), 24 h.
bCs2CO3 (0.5 mmol) was used instead of K2CO3 (0.5 mmol).
cDisulfide was detected in the reaction solution after the reaction.
dUnder Ar (1 atm). All the reaction yields were determined via GC analysis using biphenyl as an internal standard.