Optimization of the reaction conditionsa.
| ||
|---|---|---|
| Entry | Solvent | Yield (%) |
| 1 | MeCN | 90 |
| 2 | DCE | 61 |
| 3 | DMC | 86 |
| 4 | PC | Trace |
| 5 | H2O | 80 |
| 6 | 2-CH3-THF | 42 |
| 7 | EG | 19 |
| 8 | TBME | 57 |
| 9 | PEG-200 | Trace |
| 10 | PEG-400 | Trace |
| 11 | H2O : EtOH (v/v = 1 : 1) | 77 |
| 12 | H2O : EtOH (v/v = 2 : 1) | 70 |
| 13 | H2O : MeOH (v/v = 1 : 1) | 78 |
| 14 | H2O : MeOH (v/v = 2 : 1) | 72 |
| 15 | H2O : THF (v/v = 1 : 1) | 61 |
| 16 | H2O : THF (v/v = 2 : 1) | 68 |
| 17b | H2O | N.D. |
| 18c | H2O | N.D. |
| 19d | H2O | 74 |
Reaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), PIDA (0.4 mmol), solvent (2 mL) under air for 8 h, rt, 430 nm Blue LED (5 W). N.D. = Not detected. Isolated yields were given. DCE = 1,2-dichloroethane, DMC = dimethyl carbonate. TBME = tert-butyl methyl ether, EG = ethylene glycol, PC = propylene carbonate.
Without PIDA.
Experiment performed in the dark.
Reaction under N2 atmosphere.