Table 1. Optimization of Reaction Conditionsa.
entry | catalyst | cooxidant | t, time | yield of 2, % |
---|---|---|---|---|
1b | Co(OAc)2 | AgNO3 | 80 °C, 16 h | 16 |
2b | Co(acac)2 | AgNO3 | 80 °C, 16 h | 66 |
3 | Co(acac)2 | none | 80 °C, 16 h | 15 |
4c | Co(acac)2 | Mn(OAc)2 | 80 °C, 16 h | 41 |
5c | Co(acac)2 | Mn(OAc)3·2H2O | 80 °C, 16 h | 90 |
6c | none | Mn(OAc)3·2H2O | 80 °C, 16 h | <1 |
7c,d | Co(acac)2 | Mn(OAc)3·2H2O | rt, 16 h | 93 |
Amide (0.1 mmol), styrene (0.12 mmol), catalyst (0.02 mmol), base (0.2 mmol), CF3CH2OH (1 mL), under air. Yield determined by NMR of crude reaction mixtures; 1,1,2-trichloroethane internal standard.
AgNO3, 2 equiv.
Mn(OAc)2 or Mn(OAc)3·2H2O, 0.5 equiv.
Reaction open to air.