Table 1.
Optimization of the reaction conditions
| |||
| Entry | Additive | Equiv of Additive | 3a/IS GC yield (%)a |
|---|---|---|---|
| 1 | none | none | 23 |
| 2 | CS2CO3 | 1 | 43 |
| 3 | K2CO3 | 1 | 39 |
| 4 | Na2CO3 | 1 | 37 |
| 5 | K3PO4 | 1 | 30 |
| 6 | NaOAc | 1 | 18 |
| 7 | NH4OAc | 1 | 19 |
| 8b | Cs2CO3 | 1 | 52 |
| 9b | Cs2CO3 | 2 | 69 |
| 10b,c | Cs2CO3 | 2 | 87 (78d) |
| 11b,c | CsF | 2 | 63 |
| 12b,c,e | Cs2CO3 | 2 | 72 |
| 13b,c,f | Cs2CO3 | 2 | Traces |
| 14b,c, g | Cs2CO3 | 2 | no reaction |
Reaction conditions: 1a (0.1 mmol), 2a (0.1 mmol), base, dry and degassed DMSO (0.2 M) at room temperature under purple Kessil® (390 nm) irradiation for 16 h.
Calculated against 1,3,5-trimethoxybenzene as internal standard (IS).
3 equiv of 2a.
Solvent 0.13 M for 1a.
Isolated yield at 0.5 mmol scale.
Blue Kessil® (456 nm).
Green Kessil® (525 nm).
No light.