Table 3. Control Experiments for the Vitamin B12-Catalyzed Addition/1,2-Phenyl Migrationa.
| entry | deviation from the reaction conditions | yield of3a[%]b |
|---|---|---|
| 1 | - | 80 |
| 2 | no B12 | 0 |
| 3 | no Zn | 0 |
| 4 | no light | 0 |
| 5 | no B12, Zn and light | 0 |
| 6 | under air | 7 |
| 7 | no surfactant | 31 |
| 8 | no butan-1-ol | 65 |
Optimized reaction conditions: diethyl 2-phenyl-2-vinylmalonate (1, 0.10 mmol), 1-bromododecane (3 equiv, 0.30 mmol), vitamin B12 (2.5 mol %), Zn (3 equiv), DTAC (0.35 mmol), n-BuOH (1.25 mmol), H2O (5 mL), green LEDs (525 nm), 16 h, 40 °C.
Yields determined by GC analysis with mesitylene as an internal standard.
