Optimization and control reactionsa.
| ||||
|---|---|---|---|---|
| Entry | Solvent | Atm. | Time (h) | Yieldb (%) |
| 1 | Toluene | Air | 24 | 9 |
| 2 | THF | Air | 24 | 54 |
| 3 | DMSO | Air | 24 | 23 |
| 4 | DMF | Air | 24 | 52 |
| 5 | EtOAc | Air | 24 | 84 |
| 6 | DCM | Air | 24 | 56 |
| 7 | Acetone | Air | 24 | 91 |
| 8 | PEG200 | Air | 24 | 20 |
| 9 | Glycerol | Air | 24 | 5 |
| 10 | Water | Air | 24 | 57 |
| 11 | Methanol | Air | 24 | 100 |
| 12 | Ethanol | Air | 24 | 100 |
| 13c | Ethanol | Air | 24 | 0 |
| 14 | Ethanol | Nitrogen | 24 | 20 |
| 15 | Ethanol | Oxygen | 24 | 100 |
| 16 d | Ethanol | Air | 18 | 100 (89) e |
| 17d | Ethanol | Oxygen | 18 | 100 |
| 18d | Ethanol | Air | 12 | 61 |
| 19d | Ethanol | Oxygen | 12 | 94 |
Reaction conditions: 1a (0.15 mmol), 2a (0.75 equiv.), solvent (2 mL) at room temperature irradiated with 3 W blue LED (467 nm).
Yields obtained by GC using internal standard method.
Reaction performed under dark.
0.5 equiv. of 2a were used.
Isolated yield.